Fused bicyclic heterocycle derivatives as pesticides

ABSTRACT

The invention relates to novel compounds of the formula (I) or (I′) 
                         
in which R 1 , R 2 , R 3 , Aa, Ab, Ac, Ad, Ae, Q and n have the definitions given above,
 
to the use thereof as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for the preparation thereof.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a National Stage entry of International ApplicationNo. PCT/EP2016/075365, filed 21 Oct. 2016, which claims priority toEuropean Patent Application No. 15191440.5, filed 26 Oct. 2015.

BACKGROUND Field

The present invention relates to novel fused bicyclic heterocyclederivatives of the formula (I) or of the formula (I′), to the usethereof as acaricides and/or insecticides for controlling animal pests,particularly arthropods and especially insects and arachnids, and toprocesses and intermediates for the preparation thereof.

Description of Related Art

Fused bicyclic heterocycle derivatives with insecticidal properties arealready described in the literature, for example in WO 2010/125985, WO2012/074135, WO 2012/086848, WO 2013/018928, WO 2013/191113, WO2014/142292, WO 2014/148451, WO 2015/000715, EP 15153943.4, EP15153948.3 and WO 2015/121136.

Fused bicyclic heterocycle derivatives with insecticidal properties havealso already been described in the literature, for example inWO2016/091731, WO2016/039444, WO2015/198859, WO 2015/133603, WO2015/198859, WO 2015/002211, WO 2015/071180, WO 2015/091945, WO2016/005263, WO 2015/198817, WO 2016/041819, WO 2016/039441, WO2016/026848, WO 2016/023954, WO 2016/020286 and WO 2016/046071.

However, the active ingredients already known according to the documentscited above have disadvantages on application to some degree, whetherbecause they have only a narrow scope of application or because they donot have satisfactory insecticidal or acaricidal action.

SUMMARY

Novel fused bicyclic heterocycle derivatives have now been found, thesehave advantages over the compounds already known, examples of whichinclude better biological or environmental properties, a wider range ofapplication methods, better insecticidal or acaricidal action, and goodcompatibility with crop plants. The fused bicyclic heterocyclederivatives can be used in combination with further agents for improvingefficacy, especially against insects that are difficult to control.

The present invention therefore provides novel compounds of the formula(I) or (I′)

in which (configuration 1)

-   Aa is nitrogen or ═C(R⁷)—,-   Ab is nitrogen or ═C(H)—,-   Ac is nitrogen or ═C(H)—,-   Ad is nitrogen or ═C(H)—,-   Ae is nitrogen or ═C(H)—,

where Ab, Ac, Ad and Ae cannot all be nitrogen,

-   R¹ (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,    (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,    (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,    (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₅)cycloalkyl,    halo(C₃-C₈)cycloalkyl, amino, (C₁-C₆)alkylamino,    di-(C₁-C₆)alkylamino, (C₃-C₈)cycloalkylamino,    (C₁-C₆)alkylcarbonylamino, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)alkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)haloalkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonylamino,    aminosulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl,    di-(C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl,    -   or (C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl,        (C₃-C₈)cycloalkyl, each optionally mono- or polysubstituted        identically or differently by aryl, hetaryl or heterocyclyl,        where aryl, hetaryl or heterocyclyl may each optionally be mono-        or polysubstituted identically or differently by halogen, cyano,        nitro, hydroxyl, amino, carboxyl, carbamoyl, aminosulphonyl,        (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl, (C₁-C₆)alkoxy,        (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,        (C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,        (C₁-C₆)alkylsulphimino, (C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,        (C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl,        (C₁-C₆)alkylsulphoximino, (C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,        (C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl,        (C₁-C₆)alkoxycarbonyl, (C₁-C₆)alkylcarbonyl,        (C₃-C₆)trialkylsilyl or benzyl, or-   R¹ is aryl, hetaryl or heterocyclyl, each mono- or polysubstituted    identically or differently by halogen, cyano, nitro, hydroxyl,    amino, carboxyl, carbamoyl, (C₁-C₆)alkyl, (C₃-C₈)cycloalkyl,    (C₁-C₆)-alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy,    (C₁-C₆)alkylthio, (C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,    (C₁-C₆)alkylsulphimino, (C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl,    (C₁-C₆)alkylsulphoximino, (C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl,    (C₁-C₆)alkoxycarbonyl, (C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl,    (═O) (in the case of heterocyclyl only) and (═O)₂ (in the case of    heterocyclyl only),-   R², R³ are independently hydrogen, cyano, halogen, nitro, acetyl,    hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,    (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,    hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,    (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,    (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,    (C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,    (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,    (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,    (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,    (C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,    (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,    (C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,    (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,    (C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,    (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,    (C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di-(C₁-C₆)alkylaminocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,    (C₂-C₆)alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,    (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, aminosulphonyl,    (C₁-C₆)alkylaminosulphonyl, di-(C₁-C₆)alkylaminosulphonyl,    (C₁-C₆)alkylsulphoximino, aminothiocarbonyl,    (C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,    (C₃-C₈)cycloalkylamino or NHCO—(C₁-C₆)alkyl    ((C₁-C₆)alkylcarbonylamino),-   R⁷ is hydrogen, cyano, halogen, acetyl, hydroxyl, amino,    (C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,    (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₂-C₆)alkenyl,    (C₂-C₆)haloalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,    (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkylsulphinyl,    (C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkylsulphonyl or    (C₁-C₆)haloalkylsulphonyl,-   Q is a partly saturated or saturated heterocyclic or heteroaromatic    8-, 9-, 10-, 11- or 12-membered fused bicyclic or tricyclic ring    system, where at least one carbonyl group may optionally be present    and/or where the ring system is optionally mono- or polysubstituted    identically or differently, and where the substituents may    independently be selected from hydrogen, cyano, halogen, nitro,    acetyl, hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl,    (C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,    (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,    (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,    hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,    (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₄)alkyl,    (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,    (C₁-C₆)haloalkoxy, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,    (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,    (C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,    (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,    (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,    (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,    (C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,    (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,    (C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,    (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,    (C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylthiocarbonyl, (C₁-C₆)haloalkylcarbonyl,    (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,    (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)alkylaminocarbonyl,    (C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminocarbonyl,    di-(C₁-C₆)alkylaminothiocarbonyl, (C₂-C₆)alkenylaminocarbonyl,    di-(C₂-C₆)-alkenylaminocarbonyl, (C₃-C₈)cycloalkylaminocarbonyl,    (C₁-C₆)alkylsulphonylamino, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino,    aminosulphonyl, (C₁-C₆)alkylaminosulphonyl,    di-(C₁-C₆)alkylaminosulphonyl, (C₁-C₆)alkylsulphoximino,    aminothiocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di-(C₁-C₆)alkylaminothiocarbonyl, (C₃-C₈)cycloalkylamino,    NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino),    -   or where the substituents may independently be selected from        phenyl or a 5- or 6-membered heteroaromatic ring, where phenyl        or the ring may optionally be mono- or polysubstituted        identically or differently by C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,        C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl,        halogen, CN, NO₂, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,-   n is 0, 1 or 2,

where, in the case of the structural unit A4, Q is none of the followingring systems:

where X and Y, which may be the same or different, are carbon ornitrogen, R′″ is hydrogen, aldehyde, oxime or —C(O)O—R_(a), with theproviso that X is carbon, where R_(a) is C₁-C₆-alkyl, R′ and R″, whichmay be the same or different, are hydrogen, halogen, cyano, nitro,C₁-C₆-alkyl or C₁-C₆-alkoxy,

and, in addition, when Aa is ═C(H)—, in the case of the compounds of theformula (I), Q is not Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q15, Q17.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

It has additionally been found that the compounds of the formula (I) or(I′) have very good efficacy as pesticides, preferably as insecticidesand/or acaricides, and additionally generally have very good plantcompatibility, especially with respect to crop plants.

The compounds according to the invention are defined in general terms bythe formula (I) or (I′). Preferred substituents or ranges for theradicals listed in the formulae mentioned above and below areillustrated hereinafter:

Configuration 2

Aa is preferably nitrogen or ═C(R⁷)—,

Ab is preferably nitrogen or ═C(H)—,

Ac is preferably nitrogen or ═C(H)—,

Ad is preferably nitrogen or ═C(H)—,

Ae is preferably nitrogen or ═C(H)—,

where Ab, Ac, Ad and Ae cannot all be nitrogen,

preferably resulting in the following structural units A1 to A44:

-   -   where the bond to the substituent Q is identified by a wavy line        and the bond to the sulphur atom by an asterisk *,

-   R¹ is preferably (C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,    (C₃-C₆)cycloalkylamino, (C₁-C₄)alkylcarbonylamino,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylcarbonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonylamino,    -   or is (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₂-C₄)alkenyl,        (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl, each optionally mono- or        disubstituted identically or differently by aryl, hetaryl and        heterocyclyl, where aryl, hetaryl and heterocyclyl may each        optionally be mono- or disubstituted identically or differently        by halogen, cyano, carbamoyl, aminosulphonyl, (C₁-C₄)-alkyl,        (C₃-C₄)cycloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkyl,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl,        (C₁-C₄)alkylsulphonyl, (C₁-C₄)alkylsulphimino, or

-   R¹ is preferably aryl, hetaryl or heterocyclyl, each optionally    mono- or disubstituted identically or differently by halogen, cyano,    carbamoyl, (C₁-C₄)alkyl, (C₃-C₆)cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,    (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl,    (C₁-C₄)alkylsulphimino, (C₁-C₄)alkylsulphoximino,    (C₁-C₄)alkylcarbonyl, (C₃-C₄)trialkylsilyl, (═O) (in the case of    heterocyclyl only) or (═O)₂ (in the case of heterocyclyl only),

-   R², R³ are preferably independently hydrogen, cyano, halogen, nitro,    acetyl, hydroxyl, amino, SCN, tri(C₁-C₄)alkylsilyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,    (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,    (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,    (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,    (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl,    (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,    aminosulphonyl, (C₁-C₄)alkylaminosulphonyl,    di-(C₁-C₄)alkylaminosulphonyl, aminothiocarbonyl or    NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino),

-   R⁷ is preferably hydrogen, cyano, halogen, acetyl, hydroxyl, amino,    (C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₂-C₄)alkenyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,    (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,    (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl or    (C₁-C₄)haloalkylsulphonyl,

-   Q is preferably a heteroaromatic 8-, 9-, 10-, 11- or 12-membered    fused bicyclic or tricyclic ring system, where the ring system is    optionally mono- or polysubstituted identically or differently, and    where the substituents may independently be selected from hydrogen,    cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,    tri-(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,    (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,    (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl,    (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₆)haloalkynyl,    (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,    (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,    (C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,    (C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,    (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,    (C₁-C₆)haloalkyl sulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,    (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,    (C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,    (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,    (C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylthiocarbonyl, (C₁-C₆)haloalkylcarbonyl,    (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,    (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)alkylaminocarbonyl,    (C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminocarbonyl,    di-(C₁-C₆)alkylaminothiocarbonyl, (C₃-C₈)cycloalkylaminocarbonyl,    (C₁-C₆)alkylsulphonylamino, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino,    aminosulphonyl, (C₁-C₆)alkylaminosulphonyl,    di-(C₁-C₆)alkylaminosulphonyl, (C₁-C₆)alkylsulphoximino,    aminothiocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di-(C₁-C₆)alkylaminothiocarbonyl, (C₃-C₈)cycloalkylamino,    NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino),    -   or where the substituents may independently be selected from        phenyl or a 5- or 6-membered heteroaromatic ring, where phenyl        or the ring may optionally be mono- or polysubstituted        identically or differently by C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,        C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl,        halogen, CN, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,

-   n is preferably 0, 1 or 2,

where, in the case of the structural unit A4, Q is none of the followingring systems:

where X and Y, which may be the same or different, are carbon ornitrogen, R′″ is hydrogen, aldehyde, oxime or —C(O)O—R_(a), with theproviso that X is carbon, where R_(a) is C₁-C₆-alkyl, R′ and R″, whichmay be the same or different, are hydrogen, halogen, cyano, nitro,C₁-C₆-alkyl or C₁-C₆-alkoxy,

and, in addition, when Aa is ═C(H)—, in the case of the compounds of theformula (I), Q is not Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q15, Q17.

Configuration 3-1

Aa is more preferably nitrogen or ═C(R⁷)—,

Ab is more preferably nitrogen or ═C(H)—,

Ac is more preferably nitrogen or ═C(H)—,

Ad is more preferably nitrogen or ═C(H)—,

Ae is more preferably nitrogen or ═C(H)—,

where Ab, Ac, Ad and Ae cannot all be nitrogen,

-   more preferably resulting in the following structural units: A1, A2,    A3, A4, A5, A7, A8, A9, A10, A11, A12, A13, A14, A15, A17, A19, A20,    A21, A22, A23, A24, A25, A26, A27, A29, A30, A31, A32, A33, A34,    A35, A36, A37, A39, A41, A42, A43, A44,-   R¹ is more preferably (C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,-   R², R³ are more preferably independently hydrogen, cyano, halogen,    nitro, hydroxyl, amino, SCN, tri-(C₁-C₄)alkylsilyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl,    (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy,    (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,    (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkyl    sulphonyl, (C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,    di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulphonylamino,    (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino, aminosulphonyl,    (C₁-C₄)alkylaminosulphonyl, di-(C₁-C₄)alkylaminosulphonyl or    NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino),-   R⁷ is more preferably hydrogen, halogen, cyano, (C₁-C₄)alkyl or    (C₁-C₄)haloalkyl,-   Q is more preferably a heteroaromatic 9-membered or 12-membered    fused bicyclic or tricyclic ring system from the group of Q1 to Q20,

-   R⁴ is more preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,-   R⁵, R⁶ are more preferably independently hydrogen, cyano, halogen,    (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,    (C₁-C₄)haloalkyl sulphinyl, (C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkyl    sulphonyl, (C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,    di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulphonylamino,    (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino, aminosulphonyl,    (C₁-C₄)alkylaminosulphonyl or di-(C₁-C₄)alkylaminosulphonyl,-   n is more preferably 0, 1 or 2.

Configuration 3-2

Aa, Ab, Ac, Ad, Ae, R¹, R², R³, R⁷, Q, R⁵, R⁶ and n have the definitionsgiven in configuration 3-1 and

-   R⁴ is more preferably hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,

where, when Aa is ═C(H)—, in the case of the compounds of the formula(I), Q is not Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q15, Q17.

Configuration 4-1

Aa is even more preferably nitrogen or ═C(R⁷)—,

Ab is even more preferably nitrogen or ═C(H)—,

Ac is even more preferably nitrogen or ═C(H)—,

Ad is even more preferably nitrogen or ═C(H)—,

Ae is even more preferably nitrogen or ═C(H)—,

where Ab, Ac, Ad and Ae cannot all be nitrogen,

-   even more preferably resulting in the following structural units:    A1, A2, A4, A5, A7, A9, A11, A12, A13, A19, A20, A21, A22, A23, A24,    A26, A27, A29, A31, A33, A34, A35, A41, A42, A43, A44,-   R¹ is even more preferably (C₁-C₄)-alkyl, (C₁-C₄)haloalkyl or    (C₃-C₆)cycloalkyl,-   R², R³ are even more preferably independently hydrogen, cyano,    halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy,    (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl,    (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulphinyl,    (C₁-C₄)haloalkylsulphonyl or NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino),-   R⁷ is even more preferably hydrogen, halogen, cyano or (C₁-C₄)alkyl,-   Q is even more preferably a heteroaromatic 9-membered or 12-membered    fused bicyclic or tricyclic ring system from the group of Q2, Q3,    Q5, Q6, Q8, Q9, Q10, Q11, Q12, Q13, Q15, Q16, Q17, Q18, Q19 or Q20,

-   R⁴ is even more preferably (C₁-C₄)-alkyl or    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,-   R⁵ is even more preferably hydrogen, cyano, halogen, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,    (C₁-C₄)haloalkyl sulphinyl, (C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkyl    sulphonyl, (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl,    (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylaminosulphonyl or    di-(C₁-C₄)alkylaminosulphonyl,-   R⁶ is even more preferably hydrogen,-   n is even more preferably 0, 1 or 2.

Configuration 4-2

Aa, Ab, Ac, Ad, Ae, R¹, R⁵, R⁶ and n have the definitions given inconfiguration 4-1 and

-   R², R³ are independently even more preferably hydrogen, cyano,    halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkyl,    (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl,    (C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkyl    sulphinyl, (C₁-C₄)haloalkylsulphonyl or NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino),-   R⁷ is even more preferably hydrogen, halogen, cyano, (C₁-C₄)alkyl or    (C₁-C₄)haloalkyl,-   Q is even more preferably a heteroaromatic 9-membered or 12-membered    fused bicyclic or tricyclic ring system from the group of Q1, Q2,    Q3, Q5, Q6, Q8, Q9, Q10, Q11, Q12, Q13, Q15, Q16, Q17, Q18, Q19 or    Q20,-   R⁴ is even more preferably hydrogen, (C₁-C₄)alkyl or    (C₁-C₄)-alkoxy-(C₁-C₄)alkyl,

where, when Aa is ═C(H)—, in the case of the compounds of the formula(I), Q is not Q1, Q2, Q3, Q5, Q6, Q8, Q9, Q10, Q15, Q17.

Configuration 5-1

Aa is specifically nitrogen or ═C(R⁷)—,

Ab is specifically nitrogen or ═C(H)—,

Ac is specifically nitrogen or ═C(H)—,

Ad is specifically nitrogen or ═C(H)—,

Ae is specifically nitrogen or ═C(H)—,

where Ab, Ac, Ad and Ae cannot all be nitrogen,

-   specifically resulting in the following structural units: A1, A2,    A4, A11, A13, A19, A20, A23, A24, A26, A33, A35, A41, A42,-   R¹ is specifically methyl, ethyl, n-propyl, isopropyl, cyclopropyl,    n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,    trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,-   R², R³ are independently specifically hydrogen, fluorine, chlorine,    bromine, iodine, cyano, methyl, ethyl, methoxy, trifluoromethyl,    trifluoromethoxy or trifluoromethylthio,-   R⁷ is specifically hydrogen, fluorine, chlorine, bromine, cyano,    methyl, ethyl or trifluoromethyl,-   Q is specifically a hetero aromatic 9-membered fused bicyclic ring    system from the group of Q2, Q3, Q10, Q15 and Q17

-   R⁴ is specifically methyl, ethyl, isopropyl, methoxymethyl or    methoxyethyl,-   R⁵ is specifically fluorine, chlorine, bromine, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,    dichlorofluoromethoxy or trifluoromethylthio,-   R⁶ is specifically hydrogen,-   n is specifically 0, 1 or 2.

Configuration 5-2

Aa is specifically nitrogen or ═C(R⁷)—,

Ab is specifically ═C(H)—,

Ac is specifically ═C(H)—,

Ad is specifically ═C(H)—,

Ae is specifically nitrogen or ═C(H)—,

specifically resulting in the following structural units: A1, A4, A23,A26, A33,

-   R¹ is specifically methyl, ethyl, n-propyl, isopropyl, cyclopropyl,    n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,    trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,-   R², R³ are independently specifically hydrogen, fluorine, chlorine,    bromine, iodine, cyano, methyl, ethyl, methoxy, trifluoromethyl,    trifluoromethoxy or trifluoromethylthio,-   R⁷ is specifically hydrogen, fluorine, chlorine, bromine, cyano,    methyl, ethyl or trifluoromethyl,-   Q is specifically a heteroaromatic 9-membered or 12-membered fused    bicyclic ring system from the group of Q1, Q2, Q3, Q16, Q17 or Q20,-   R⁴ is specifically hydrogen, methyl, ethyl, isopropyl, methoxymethyl    or methoxyethyl,-   R⁵ is specifically fluorine, chlorine, bromine, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),    difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl, (CH₂CF₃,    CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,    dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl    or trifluoromethylsulphanyl,-   R⁶ is specifically hydrogen,-   n is specifically 0, 1 or 2,

where, when Aa is ═C(H)—, in the case of the compounds of the formula(I), Q is not Q1, Q2, Q3, Q17.

Configuration 6-1

Aa is especially nitrogen or ═C(R⁷)—,

Ab is especially ═C(H)—,

Ac is especially ═C(H)—,

Ad is especially ═C(H)—,

Ae is especially ═C(H)—,

especially resulting in the following structural units: A1 or A4,

-   R¹ is especially ethyl,-   R², R³ are especially hydrogen,-   R⁷ is especially hydrogen,-   Q is especially a heteroaromatic 9-membered fused bicyclic ring    system from the group of Q3

-   R⁴ is especially methyl,-   R⁵ is especially trifluoromethyl,-   R⁶ is especially hydrogen,-   n is especially 0 or 2.

Configuration 6-2

Aa is especially nitrogen or ═C(R⁷)—,

Ab is especially ═C(H)—,

Ac is especially ═C(H)—,

Ad is especially ═C(H)—,

Ae is especially nitrogen or ═C(H)—,

especially resulting in the following structural units: A1, A4, A23,A26, A33

-   R¹ is especially methyl or ethyl,-   R² is especially hydrogen, chlorine, methoxy or trifluoromethyl,-   R³ is especially hydrogen,-   R⁷ is especially hydrogen,-   Q is especially a heteroaromatic 9-membered or 12-membered fused    bicyclic ring system from the group of Q1, Q2, Q3, Q16, Q17, Q20,-   R⁴ is especially hydrogen or methyl,-   R⁵ is especially trifluoromethyl or pentafluoroethyl,-   R⁶ is especially hydrogen,-   n is especially 0, 1 or 2,

where, when Aa is ═C(H)—, in the case of the compounds of the formula(I), Q is not Q1, Q2, Q3, Q17.

Configuration 6-3

Aa is especially nitrogen or ═C(R⁷)—,

Ab is especially ═C(H)—,

Ac is especially ═C(H)—,

Ad is especially ═C(H)—,

Ae is especially nitrogen or ═C(H)—,

preferably resulting especially in the following structural units: A23,A26, A33,

-   R¹ is especially methyl or ethyl,-   R² is especially hydrogen or trifluoromethyl,-   R³ is especially hydrogen,-   R⁷ is especially hydrogen,-   Q is especially a ring system from the group of Q1, Q2, Q3, Q17,-   R⁴ is especially methyl,-   R⁵ is especially trifluoromethyl or pentafluoroethyl,-   R⁶ is especially hydrogen,-   n is especially 0, 1 or 2,

where, when Aa is ═C(H)—, in the case of the compounds of the formula(I), Q is not Q1, Q2, Q3, Q17.

With inclusion of structural units A1 to A44, this results in thefollowing principal structures of the formula (I) or formula (I′):

where R¹, R², R³, R², Q and n have the definitions given above.

In a preferred embodiment, the invention relates to compounds of theformula (I) where R¹, R², R³, R², Q, Aa, Ab, Ac, Ad, Ae and n have thedefinitions given in configuration (1) or configuration (2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Q, Aa, Ab, Ac, Ad, Ae andn have the definitions given in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where R¹, R², R³, R⁷, Q, Aa, Ab, Ac, Ad, Ae and n have thedefinitions given in configuration (1) or configuration (2).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Q, Aa, Ab, Ac, Ad, Ae andn have the definitions given in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q1 and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Aa, Ab, Ac,Ad, Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q2 and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Aa, Ab, Ac,Ad, Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q3 and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Aa, Ab, Ac,Ad, Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q4 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad, Aeand n have the definitions given in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q5 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad, Aeand n have the definitions given in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q6 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad, Aeand n have the definitions given in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q7 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad, Aeand n have the definitions given in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q8 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad, Aeand n have the definitions given in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q9 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad, Aeand n have the definitions given in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q10 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q11 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q12 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q13 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q14 and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Aa, Ab, Ac,Ad, Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q15 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q16 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q17 and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Aa, Ab, Ac,Ad, Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q18 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q19 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q20 and R¹, R², R³, R⁴, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q1 and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Aa, Ab, Ac,Ad, Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q2 and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Aa, Ab, Ac,Ad, Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q3 and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Aa, Ab, Ac,Ad, Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q4 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q5 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q6 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q7 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q8 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q9 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q10 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q11 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q12 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q13 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q14 and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Aa, Ab, Ac,Ad, Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q15 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q16 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q17 and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Aa, Ab, Ac,Ad, Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q18 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q19 and R¹, R², R³, R⁵, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where Q is Q20 and R¹, R², R³, R⁴, R⁶, R⁷, Aa, Ab, Ac, Ad,Ae and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) with the structural unit A1 and where Q is Q16 or Q20 andR¹, R², R³, R⁴, R⁵, R⁶, R⁷ and n have the definitions given inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) with the structural unit A4 and where Q, R¹, R², R³, R⁴, R⁵,R⁶ and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) with the structural unit A23 and where Q, R¹, R², R³, R⁴,R⁵, R⁶, R⁷ and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) with the structural unit A26 and where Q, R¹, R², R³, R⁴,R⁵, R⁶ and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) with the structural unit A33 and where Q, R¹, R², R³, R⁴,R⁵, R⁶, R⁷ and n have the definitions given in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I′) where

Aa is nitrogen or ═C(R⁷)—,

Ab is ═C(H)—,

Ac is ═C(H)—,

Ad is ═C(H)—,

Ae is nitrogen or ═C(H)—,

preferably resulting in the following structural units: A23, A26, A33,

-   R¹ is methyl or ethyl,-   R² is hydrogen or trifluoromethyl,-   R³ is hydrogen,-   R⁷ is hydrogen,-   Q is a ring system from the group of Q1, Q2, Q3, Q17,-   R⁴ is methyl,-   R⁵ is trifluoromethyl or pentafluoroethyl,-   R⁶ is hydrogen,-   n is 0, 1 or 2.

In a preferred embodiment, the invention relates to compounds of formula(I) or (I′) where Q is the following ring systems:

where R⁶ is hydrogen and R¹, R², R³, R⁴, R⁵, R⁷, Aa, Ab, Ac, Ad, Ae andn have the definitions given in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3).

In the preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,

In the particularly preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,

In the context of the present invention, unless defined differentlyelsewhere, the term “alkyl”, either on its own or else in combinationwith further terms, for example haloalkyl, is understood to mean aradical of a saturated aliphatic hydrocarbon group which has 1 to 12carbon atoms and may be branched or unbranched. Examples of C₁-C₁₂-alkylradicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl,n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. Amongthese alkyl radicals, particular preference is given to C₁-C₆-alkylradicals. Special preference is given to C₁-C₄-alkyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkenyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkenylradical which has at least one double bond, for example vinyl, allyl,1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl,1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyland 1,4-hexadienyl. Among these, preference is given to C₂-C₆-alkenylradicals and particular preference to C₂-C₄-alkenyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkynyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkynylradical which has at least one triple bond, for example ethynyl,1-propynyl and propargyl. Among these, preference is given toC₃-C₆-alkynyl radicals and particular preference to C₃-C₄-alkynylradicals. The alkynyl radical may also contain at least one double bond.

According to the invention, unless defined differently elsewhere, theterm “cycloalkyl”, either on its own or else in combination with furtherterms, is understood to mean a C₃-C₈-cycloalkyl radical, for examplecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl. Among these, preference is given to C₃-C₆-cycloalkylradicals.

The term “alkoxy”, either on its own or else in combination with furtherterms, for example haloalkoxy, is understood to mean an O-alkyl radical,where the term “alkyl” is as defined above.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms may be identical ordifferent. In this case, halogen is fluorine, chlorine, bromine oriodine, especially fluorine, chlorine or bromine.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, where the substituents in the case of polysubstitutionsmay be the same or different.

The radical definitions or elucidations given above in general terms orwithin areas of preference apply to the end products and correspondinglyto the starting materials and intermediates. These radical definitionscan be combined with one another as desired, i.e. including combinationsbetween the respective ranges of preference.

Preference is given in accordance with the invention to using compoundsof the formula (I) or (I′) in which a combination of the definitionslisted above as being preferred is present.

Particular preference is given in accordance with the invention to usingcompounds of the formula (I) or (I′) in which a combination of thedefinitions listed above as being more preferred is present.

Very particular preference is given in accordance with the invention tousing compounds of the formula (I) or (I′) in which a combination of thedefinitions listed above as being even more preferred is present.

Specific preference is given in accordance with the invention to usingcompounds of the formula (I) or (I′) in which a combination of thedefinitions listed above as being specifically preferred is present.

Especial preference is given in accordance with the invention to usingcompounds of the formula (I) or (I′) in which a combination of thedefinitions listed above as being especially preferred is present.

Depending on the nature of the substituents, the compounds of theformula (I) or (I′) may be in the form of geometric and/or opticallyactive isomers or corresponding isomer mixtures in differentcompositions.

These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. The invention therefore encompassespure stereoisomers and any desired mixtures of these isomers.

The compounds of the formula (I) or (I′) according to the invention canbe obtained by the processes shown in the following schemes:

Process A-1

The compounds of the formula (I) in which Q is Q1 to Q9 or Q20 can beprepared by known methods, for example analogously to the processesdescribed in WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629,WO2012/086848, WO2013/018928, WO2015/000715, WO2015/198859,WO2016/039444, WO2016/039441, WO2016/116338 and WO2015/121136.

The radicals R¹, R², R³, R⁴, R⁵, R⁶, Aa, Ab, Ac, Ad, Ae and n have thedefinitions described above, A² and A³ are CH or N (where A² and A³ maynot both be N), A⁴ is O—H, S—H or N(H)R⁴, A⁴ may also be chlorine, andX¹ is halogen.

Step a)

The compounds of the formula (IV) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,576,335 by the reaction ofcompounds of the formula (II) with carboxylic acids of the formula (III)in the presence of a condensing agent or a base.

Compounds of the formula (II) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in US2003/69257, WO2006/65703, WO2009/131237, WO2010/125985,WO2011/043404, WO2011/040629, WO2012/086848, WO2013/018928 orWO2015/000715.

Carboxylic acids of the formula (III) are either commercially availableor can be prepared by known methods. Possible preparation routes aredescribed in process F.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (III) can be effected neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogen-containingcompounds, for example pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Particularpreference is given here to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium hydrogencarbonate, potassium hydrogencarbonate.

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of 0° C. to 180°C.; with preference, the reaction is carried out at standard pressureand temperatures of 20 to 140° C.

Step b)

The compounds of the formula (V) can be prepared by condensing thecompounds of the formula (IV), for example analogously to the processesdescribed in WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629,WO2012/086848, WO2013/018928, WO2015/000715 and WO2015/121136.

The conversion to compounds of the formula (V) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction can be conducted in the presence of a condensing agent, anacid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulphonic acids such as para-toluenesulphonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

The compounds of the formula (I) where n represents 0 can be prepared byreacting the compounds of the formula (V) with the compounds of theformula (VIa) in the presence of a base.

Mercaptan derivatives of the formula (VIa), for example methylmercaptan, ethyl mercaptan or isopropyl mercaptan, are eithercommercially available or can be prepared by known methods, for exampleanalogously to the processes described in US2006/25633, US2006/111591,U.S. Pat. No. 2,820,062, Chemical Communications, 13 (2000), 1163-1164or Journal of the American Chemical Society, 44 (1922), p. 1329.

The conversion to compounds of the formula (I) where n is 0 can beeffected neat or in a solvent, preference being given to conducting thereaction in a solvent selected from customary solvents that are inertunder the prevailing reaction conditions. Preference is given to ethers,for example diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulphoxide.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given here to caesium carbonate, sodiumcarbonate and potassium carbonate. Further suitable bases are alkalimetal hydrides, for example sodium hydride.

Alternatively, it is possible to directly use the salts of the mercaptanderivatives, for example sodium ethanethiolate, sodium methanethiolateor sodium isopropanethiolate, without addition of further base. Thereaction can be conducted under reduced pressure, at standard pressureor under elevated pressure, and at temperatures of 0° C. to 200° C.

In the reaction described, X¹ is preferably a fluorine or chlorine atom.

If R² or R³ is likewise halogen (for example chlorine or fluorine), forexample with use of methyl mercaptan, ethyl mercaptan or isopropylmercaptan, it is also possible for multiple exchange with the alkylmercaptan to take place as well as the single substitution of X¹.

Step d)

The compounds of the formula (I) where n is 1 can be prepared byoxidizing the compounds of the formula (I) where n is 0. The oxidationis generally conducted in a solvent selected from customary solventswhich are inert under the prevailing reaction conditions. Preference isgiven to halogenated hydrocarbons, for example dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene;alcohols such as methanol or ethanol; formic acid, acetic acid,propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide,meta-chloroperbenzoic acid or sodium periodate.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step e)

The compounds of the formula (I) where n is 2 can be prepared byoxidizing the compounds of the formula (I) where n is 1. The oxidationis generally conducted in a solvent. Preference is given to halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such asmethanol or ethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step f)

The compounds of the formula (I) where n is 2 can also be prepared in aone-step process by oxidizing the compounds of the formula (I) where nis 0. The oxidation is generally conducted in a solvent. Preference isgiven to halogenated hydrocarbons, for example dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene;alcohols such as methanol or ethanol; formic acid, acetic acid,propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

The compounds of the formula (I′) in which Q is Q1 to Q9 or Q20 canlikewise be prepared analogously to process A-1, proceeding from thecorresponding carboxylic acids of the formulae (III′^(-A)) or(III′^(-B)), the possible preparation routes for which are described inprocesses G and H.

If R² or R³ is likewise alkylsulphanyl, it is possible with use of asuitable oxidizing agent, for example hydrogen peroxide andmeta-chloroperbenzoic acid, as well as the oxidation of the sulphur atomalongside R¹ to the sulphone, for oxidation of the alkylsulphanylsubstituent to alkylsulphonyl to take place in addition.

Process A-2

The radicals Aa, Ab, Ac, Ad, Ae, R¹, R², R³, R⁵, R⁶ and n have thedefinitions described above, A² and A³ are CH or N, X¹ is halogen, A⁴ isO—H, S—H or N(H)R⁴, A⁴ may also be chlorine, and R⁸ is (C₁-C₄)alkyl.

Step a)

The compounds of the formulae (XXXII) and (XXXIII) can be prepared byreacting the compounds of the formula (XXXI) with the compounds of theformula (VIa) in the presence of a base.

The compounds of the formula (XXXI) are either commercially available orcan be prepared by known methods, for example from 2-aminopyridinederivatives analogously to the processes described in WO2011/41713 or inanalogy to processes F-1 and F-2.

Mercaptan derivatives of the formula (VIa), for example methylmercaptan, ethyl mercaptan or isopropyl mercaptan, are eithercommercially available or can be prepared by known methods, for exampleanalogously to the processes described in US2006/25633, US2006/111591,U.S. Pat. No. 2,820,062, Chemical Communications, 13 (2000), 1163-1164or Journal of the American Chemical Society, 44 (1922), p. 1329.

The conversion to compounds of the formulae (XXXII) and (XXXIII) can beeffected neat or in a solvent; preferably, the reaction is conducted ina solvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulphoxide.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given here to caesium carbonate, sodiumcarbonate and potassium carbonate. Further suitable bases are alkalimetal hydrides, for example sodium hydride.

Alternatively, it is possible to directly use the salts of the mercaptanderivatives, for example sodium ethanethiolate, sodium methanethiolateor sodium isopropanethiolate, without addition of further base.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step b)

The compounds of the formula (XXXIIIb) can be prepared by oxidizing thecompounds of the formula (XXXIII). The oxidation is generally conductedin a solvent. Preference is given to halogenated hydrocarbons, forexample dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; alcohols such as methanol orethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

The compounds of the formula (XXXIIIa) can be prepared analogously byoxidizing the compounds of the formula (XXXIII).

The compounds of the formula (XXXIIIa) can be prepared analogously byoxidizing the compounds of the formula (XXXIIIb).

Step c)

The compounds of the formula (XXXIV) where n is 2 can be prepared byhydrolysing the compounds of the formula (XXXIIIa) in the presence of abase. The hydrolysis is generally conducted in a solvent. Preference isgiven to alcohols such as methanol or ethanol; water; ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulphoxide; ormixtures of the solvents mentioned.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given here to caesium carbonate, sodiumcarbonate and potassium carbonate.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to200° C.

The compounds of the formula (XXXIV) where n is 0 can analogously beprepared by hydrolysing the compounds of the formula (XXXIII).

The compounds of the formula (XXXIV) where n is 1 can analogously beprepared by hydrolysing the compounds of the formula (XXXIIIb).

The further conversion of compounds of the formula (XXXIV) to compoundsof the formula (I) is carried out analogously to process A-1.

Step d)

The compounds of the formula (XXXV) can be prepared by the reaction ofcompounds of the formula (II) with carboxylic acids of the formula(XXXIV) in the presence of a condensing agent or a base.

The compounds of the formula (II) are either commercially available orcan be prepared by known methods, for example analogously to theprocesses described in US2003/069257, US2012/0319050, WO2011/107998 orWO2010/91310.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (XXXIV) where n is 0, 1 or 2 can be effected neat or in asolvent, preference being given to conducting the reaction in a solventselected from customary solvents that are inert under the prevailingreaction conditions. Preference is given to ethers, for examplediisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane;halogenated hydrocarbons, for example dichloromethane, chloroform,carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogen-containingcompounds, for example pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI),1,3-dicyclohexylcarbodiimide, thionyl chloride or oxalyl chloride.

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Particularpreference is given here to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium hydrogencarbonate, potassium hydrogencarbonate. Further suitablebases are alkali metal hydrides, for example sodium hydride.

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of 0° C. to 180°C.; with preference, the reaction is carried out at standard pressureand temperatures of 20 to 140° C.

Step e)

The compounds of the formula (I) where n is 0, 1 or 2 can be prepared bycondensing the compounds of the formula (XXXV) in the presence of abase.

The conversion to compounds of the formula (I) where n is 0, 1 or 2 canbe effected neat or in a solvent, preference being given to conductingthe reaction in a solvent selected from customary solvents that areinert under the prevailing reaction conditions. Preference is given toethers, for example diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Particularpreference is given here to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium hydrogencarbonate, potassium hydrogencarbonate.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

The compounds of the formula (I′) in which Q is Q1 to Q9 or Q20 canlikewise be prepared analogously to process A-2.

Process B

The compounds of the formula (I) in which Q represents Q10, Q11, Q15 orQ16 can be prepared by known methods, for example analogously to theprocesses described in US2009/203705, US2012/258951, WO2013/3298,WO2016/071214 or J. Med. Chem. 31, (1988) 1590-1595.

The radicals R¹, R², R³, R⁵, R⁶, Aa, Ab, Ac, Ad, Ae and n have thedefinitions described above. A², A³, A⁴ and A⁵ are CH or N (where A²,A³, A⁴ and A⁵ are not all N) and X¹ is halogen.

Step a)

Carboxylic acids of the formula (III) are converted in analogy to theprocess described in WO2011/75643 or EP2671582 in the presence ofO,N-dimethylhydroxylamine hydrochloride to Weinreb amides of the formula(VI).

Carboxylic acids of the formula (III) are either commercially availableor can be prepared by known methods. Possible preparation routes aredescribed in process F.

Step b, c)

Compounds of the formula (VI) can then be converted by known methods,for example in analogy to the process described in WO2011/75643, with aGrignard reagent, for example methylmagnesium bromide, to ketones of theformula (VII). Compounds of the formula (VIII) are obtainable bysubsequent halogenation analogously, for example, to the known methoddescribed in US2012/302573.

Step d)

The compounds of the formula (X) can be prepared by cyclizing thecompounds of the formula (VIII) with amines of the formula (IX). Thecyclization is effected, for example, in ethanol, acetonitrile orN,N-dimethylformamide by known methods in analogy, for example, to theprocesses described in WO2005/66177, WO2012/88411, WO2013/3298,US2009/203705, US2012/258951, WO2012/168733, WO2014/187762 or J. Med.Chem. 31 (1988) 1590-1595.

The compounds of the formula (IX) are commercially available.

Step e)

The compounds of the formula (I) where n is 0 can be prepared byreacting the compounds of the formula (X) with the compounds of theformula (VIa) in the presence of a base. Mercaptan derivatives of theformula (VIa), for example methyl mercaptan, ethyl mercaptan orisopropyl mercaptan, are either commercially available or can beprepared by known methods, for example analogously to the processesdescribed in US2006/25633, US2006/111591, U.S. Pat. No. 2,820,062,Chemical Communications, 13 (2000), 1163-1164 or Journal of the AmericanChemical Society, 44 (1922), p. 1329.

Alternatively, it is possible to directly use the salts of the mercaptanderivatives, for example sodium ethanethiolate, sodium methanethiolateor sodium isopropanethiolate, without addition of further base.

Step f, g)

The compounds of the formula (I) where n is 1 can be prepared byoxidizing the compounds of the formula (I) where n is 0. The oxidationis effected by known methods using a suitable oxidizing agent, forexample hydrogen peroxide, meta-chloroperbenzoic acid or sodiumperiodate.

The compounds of the formula (I) where n is 2 can be prepared byoxidizing the compounds of the formula (I) where n is 1.

The oxidation is generally conducted in a solvent. Preference is givento halogenated hydrocarbons, for example dichloromethane, chloroform,carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols suchas methanol or ethanol; formic acid, acetic acid, propionic acid orwater. Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

Step h)

The compounds of the formula (I) where n is 2 can also be prepared in aone-step process by oxidizing the compounds of the formula (I) where nis 0. The oxidation is generally conducted in a solvent. Preference isgiven to halogenated hydrocarbons, for example dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene;alcohols such as methanol or ethanol; formic acid, acetic acid,propionic acid or water. Examples of suitable oxidizing agents arehydrogen peroxide and meta-chloroperbenzoic acid.

The compounds of the formula (I′) in which Q is Q10, Q11, Q15 and Q16can likewise be prepared analogously to process B.

Process C

The compounds of the formula (I) in which Q represents Q17 can beprepared by known methods, for example analogously to the processesdescribed in WO2014/142292.

The radicals R², R³, R⁴, R⁵, R⁶, Aa, Ab, Ac, Ad and Ae have thedefinitions described above. X¹ is halogen.

Step a)

The compounds of the formula (XI) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,374,646 or Bioorganic and MedicinalChemistry Letters 2003, 13, 1093-1096 by reacting compounds of theformula (III) with an ammonia source in the presence of a condensingagent.

Carboxylic acids of the formula (III) are either commercially availableor can be prepared by known methods. Possible preparation routes aredescribed in process F.

The reaction of the compounds of the formula (III) with the ammoniasource is preferably conducted in a solvent selected from customarysolvents which are inert under the prevailing reaction conditions.Preference is given to ethers, for example dioxane or tetrahydrofuran.

A suitable condensing agent is, for example, carbonyldiimidazole.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure. Preferably, the reaction is carriedout at atmospheric pressure and temperatures from 20 to 70° C.

Step b)

The compounds of the formula (XIII) can be prepared in analogy to theprocess described in WO2014/142292 by reacting compounds of the formula(XI) with compounds of the formula (XII) in the presence of a palladiumcatalyst in basic media.

Compounds of the formula (XII) can be prepared, for example, analogouslyto the processes described in WO2014/142292. A palladium catalyst usedmay, for example, be[1,1′-bis-(diphenylphosphino)ferrocene]dichloropalladium(II).Frequently, the bases used are inorganic bases such as potassiumtert-butoxide.

The reaction is effected in a solvent. Frequently, toluene is used.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure. Preferably, the reaction is carriedout at atmospheric pressure and temperatures from 20 to 110° C.

The further conversion of compounds of the formula (XIII) to compoundsof the formula (I) is carried out analogously to process A.

The compounds of the formula (I′) in which Q is Q17 can likewise beprepared analogously to process C.

Process D

The compounds of the formula (I) in which Q is Q14 can be prepared byknown methods, for example analogously to the processes described inWO2011/073149.

The radicals R², R³, R⁴, R⁵, R⁶, Aa, Ab, Ac, Ad and Ae have thedefinitions described above. X′ is halogen.

Step a)

The compounds of the formula (XV) can be prepared in analogy to theprocess described in WO2011/073149 or U.S. Pat. No. 5,576,335 by thereaction of compounds of the formula (XIV) with a carboxylic acid of theformula (III) in the presence of a condensing agent or a base.

Compounds of the formula (XIV) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in WO2008/51493 or in Bioorganic and Medicinal Chemistry 2014,22, 13, 3515-3526.

Carboxylic acids of the formula (III) are either commercially availableor can be prepared by known methods. Possible preparation routes aredescribed in process F.

The reaction of the compounds of the formula (XIV) with carboxylic acidsof the formula (III) can be effected neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogen-containingcompounds, for example pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Particularpreference is given here to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium hydrogencarbonate, potassium hydrogencarbonate.

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of 0° C. to 180°C.; with preference, the reaction is carried out at standard pressureand temperatures of 20 to 140° C.

Step b)

The compounds of the formula (XVI) can be prepared by condensing thecompounds of the formula (XV), for example analogously to the processesdescribed in WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629,WO2012/086848, WO2013/018928 or WO2015/000715.

The conversion to compounds of the formula (XVI) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction can be conducted in the presence of a condensing agent, anacid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulphonic acids such as para-toluenesulphonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

The further conversion of compounds of the formula (XVI) to compounds ofthe formula (I) is carried out analogously to process A.

The compounds of the formula (I′) in which Q is Q14 can likewise beprepared analogously to process D.

Process E

The compounds of the formula (I) in which Q represents Q12, Q13, Q18 orQ19 can be prepared by known methods, for example analogously to theprocesses described in WO2010/091310, WO 2012/66061 or WO2013/099041.

The radicals R², R³, R⁵, R⁶, Aa, Ab, Ac, Ad and Ae have the definitionsdescribed above. A², A³ and A⁶ are CH or N (where A² and A³ cannot bothbe N). X¹ and X² are halogen.

Step a)

The compounds of the formula (XIX) can be prepared by reacting compoundsof the formula (XVII) with compounds of the formula (XVIII) under basicconditions, for example analogously to the processes described inWO2010/091310, WO 2012/66061, WO2013/099041 or Tetrahedron 1993, 49,10997-11008.

Compounds of the formula (XVII) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in WO2005/100353, WO 2012/66061 or in European Journal ofMedicinal Chemistry 2010, 45, 2214-2222.

Compounds of the formula (XVIII) are either commercially available orcan be prepared by known methods, for example analogously to theprocesses described in WO2013/43518, EP2168965 or in Journal ofMedicinal Chemistry 2003, 46, 1449-1455.

The bases used are usually inorganic bases such as sodium hydride,potassium carbonate or caesium carbonate.

The conversion to compounds of the formula (XIX) is usually effected ina solvent, preferably in a nitrile, for example acetonitrile orpropionitrile, or in an aprotic polar solvent, for exampleN,N-dimethylformamide or N-methylpyrrolidone.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Alternatively, the reaction of compounds of the formula (XVII) withcompounds of the formula (XVIII) to give compounds of the formula (XIX)can also be effected by palladium-catalysed N-arylation, e.g.analogously to the processes described in Angewandte Chemie Int. Ed.2011, 50, 8944-8947.

The further conversion of compounds of the formula (XIX) to compounds ofthe formula (I) is effected analogously to process A.

The compounds of the formula (I′) in which Q is Q12, Q13, Q18 and Q19can likewise be prepared analogously to process E.

Process F-1

Carboxylic acids of the formula (III) are either commercially availableor can be prepared by known methods, for example from aminoaryl,diaminoaryl, aminohetaryl or diaminohetaryl derivatives in analogy tothe methods described in Journal of the American Chemical Society, 137(2015), 6168-6171; Journal of the American Chemical Society, 137 (2015),2996-3003; Synlett, 3 (2006), 379-382; Organic Letters, 14, (2012),836-839; Indian Journal of Chemistry, Section B: Organic ChemistryIncluding Medicinal Chemistry, 22B (1983), 178-179; Journal of OrganicChemistry, 55 (1990), 2838-2842; Tetrahedron Letters, 41 (2000),8053-8057; US2013/0225552; Organic Reactions (Hoboken, N.J., UnitedStates), 28, 1982; WO2011/150156; JP2009/173589; SyntheticCommunications 41 (2011), 1843-1851; Journal of the Chemical Society,(1954), 1879-1882; Heterocycles, 60 (2003), 953-957; Organic &Biomolecular Chemistry, 5 (2007), 61-64; Chemical Communications, 2(2002), 180-181; Tetrahedron Letters, 48 (2007), 5371-5374; Chemistry—AEuropean Journal, 20 (2014), 5569-5572; CN103420927, Medicinal ChemistryResearch, 22 (2013), 1660-1673; Medicinal Chemistry Letters, 6 (2015),282-286 and WO2015/071178.

The radicals R², R³, Aa, Ab, Ac, Ad and Ae have the definitionsdescribed above. B is hydrogen, halogen, NH₂ or CHO. X¹ is halogen andY¹ is halogen, methyl, C(O)OR⁸ or cyano. R⁸ is hydrogen or C₁-C₆-alkyl.

Step a)

The compounds of the formula (XXI) in which Aa is N can be prepared inanalogy to the processes described in Tetrahedron Letters, 48 (2007),5371-5374; Chemistry—A European Journal, 20 (2014), 5569-5572;CN103420927; Medicinal Chemistry Research, 22 (2013), 1660-1673;Medicinal Chemistry Letters, 6 (2015), 282-286, by the reaction ofcompounds of the formula (XX) in which B is NH₂ with a carbonyl compoundunder basic, acidic or thermal conditions.

The compounds of the formula (XXI) in which Aa is CR⁷ can be prepared inanalogy to the processes described in Journal of the American ChemicalSociety, 137 (2015), 6168-6171; Journal of the American ChemicalSociety, 137 (2015), 2996-3003; Synlett, 3 (2006), 379-382; OrganicLetters, 14, (2012), 836-839; Tetrahedron Letters, 41 (2000), 8053-8057;US2013/0225552; Organic Reactions (Hoboken, N.J., United States), 28,1982; WO2011/150156; Synthetic Communications 41 (2011), 1843-1851;Journal of the Chemical Society, (1954), 1879-1882; Organic &Biomolecular Chemistry, 5 (2007), 61-64, by a condensation andsubsequent cyclization of compounds of the formula (XX) in which B ishydrogen, halogen or CHO with a suitable carbonyl compound or acarboxylic acid derivative under basic, acidic or thermal conditions.The further functionalization in the 4 position for introduction ofradicals of the R⁷ type hydrogen) can be achieved, for example asdescribed in WO2013/066736 via a halogenation; as described in PracticalMethods for Biocatalysis and Biotransformations 2, (2012), 153-157 via ahydroxylation; as described in Organometallics, 9 (1990), 1778-1784 viaan alkylation; as described in Journal of Heterocyclic Chemistry, 22(1985), 353-355 via an amination, or as described in WO2010/020981 via anitration.

The compounds of the formula (XX) are either commercially available orcan be prepared by known methods, for example in analogy to the methodsdescribed in Chemical Reviews, 12 (1933), 43-179; Chemical Reviews, 57(1957), 525-581; Journal of Organic Chemistry, 15 (1950), 1224-1232;Recueil Travaux Chimiques des Pays-Bas et de la Belgique, 69 (1950),468-673; Journal of Chemical Technology and Biotechnology, 37 (1987),195-202; WO2012/117000; Chemistry—A European Journal, 18 (2012),16358-16368; Journal of Organic Chemistry, 48 (1983), 1064-1069; OrganicSynthesis, 44 (1964), 34-39; Journal of Heterocyclic Chemistry, 23(1986), 669-672; Bioorganic & Medicinal Chemistry Letters, 18 (2008),5023-5026; Journal of Organic Chemistry, 48 (1983), 3401-3408; Journalof Heterocyclic Chemistry, 48 (2011), 1383-1387; WO2003/051366;Helvetica Chimica Acta, 18 (1935), 1229-1239; Synthesis, 1 (1978),23-24; Organic Synthesis, 19 (1939), 70-72; Canadian Journal ofChemistry, 38 (1960), 2363-2366; Journal of Organic Chemistry, 42(1977), 3491-3496.

Step b)

Compounds of the formula (XXII) can be prepared by known methods, forexample via a hydrolysis of compounds of the formula (XXI) (ifY¹═C(O)OR⁸ or cyano) under acidic, basic or thermal conditions.

Compounds of the formula (XXII) can be prepared in analogy to theprocesses described in Synlett, 3 (2006), 379-382; Indian Journal ofChemistry, Section B: Organic Chemistry Including Medicinal Chemistry,22B (1983), 178-179; Journal of Organic Chemistry, 55 (1990), 2838-2842;Heterocycles, 60 (2003), 953-957; Chemical Communications, 2 (2002),180-181 and WO2015/071178, via a benzylic oxidation from compounds ofthe formula (XXI) (if Y′=methyl).

Compounds of the formula (XXII) can be prepared in analogy to theprocesses described in Journal of the American Chemical Society, 135(2013), 2891-2894; Synlett, 11 (2006), 1663-1666; Helvetica ChimicaActa, 55 (1972), 2295-2300; WO2013/149997 and European Journal ofOrganic Chemistry, 29 (2014), 6418-6430 via a carbonylation (R⁸=alkyl)or a carboxylation (R⁸=hydrogen) from compounds of the formula (XXI) (ifY¹=halogen).

Step c)

Compounds of the formula (III) can be prepared by known methods fromcompounds of the formula (XXII) via a halogenation. This can beeffected, for example, via a directed ortho-lithiation, followed bycapture of the carbanion with a suitable electrophilic halogenatingreagent or alternatively via a carboxylic acid derivative-directedhalogenation in analogy to the processes described in Bioorganic &Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58(2002), 6723-6728 and WO2003/010146.

If R⁸ is C₁-C₆-alkyl, the corresponding carboxylic esters of the formula(XXII), after the halogenation, can be hydrolysed under acidic or basicconditions in a polar protic solvent, such as ethanol or methanol, or apolar aprotic solvent, such as tetrahydrofuran, using, for example,dilute hydrochloric acid or alkali metal hydroxides, to the carboxylicacids of the formula (III).

Process F-2

The radicals R², R³, Aa, Ab, Ac, Ad and Ae have the definitionsdescribed above. X¹ is halogen. R⁸ is C₁-C₆-alkyl.

Step a)

Compounds of the formula (XXII) are either commercially available or canbe obtained in analogy to the processes described in ChemSusChem 2015,8, 1916-1925, Chemical Engineering Journal 2015, 271, 269-275, CatalysisCommunications 2015, 59, 122-126, Synthetic Communications 2014, 44,2386-2392, Synthetic Communications 2014, 44, 836-846, Journal ofOrganic Chemistry 2013, 78, 11606-11611, Organic Letters 2011, 13,320-323 and Journal of the American Chemical Society 1948, 70, 3135-3136from the corresponding carboxylic acids of the formula (XXX) via anesterification or alkylation under acidic or neutral conditions.

The compounds of the formula (XXX) are commercially available or can beprepared via a hydrolysis from compounds of the formula (XXII).

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of 0° C. to 180°C.; with preference, the reaction is carried out at standard pressureand temperatures of 20 to 140° C.

Step b)

Compounds of the formula (XXXI) can be prepared by known methods fromcompounds of the formula (XXII) via a halogenation. This can beeffected, for example, via a directed ortho-lithiation, followed bycapture of the carbanion with a suitable electrophilic halogenatingreagent or alternatively via a carboxylic acid derivative-directedhalogenation in analogy to the processes described in Bioorganic &Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58(2002), 6723-6728 and WO2003/010146.

Step c)

The compounds of the formula (III) are either commercially available orcan be synthesized in analogy to the processes described in Synthesis1987, 6, 586-587, Tetrahedron Letters 2006, 47, 565-567 or ChemMedChem2010, 5, 65-78 via a hydrolysis from the compounds of the formula(XXXI).

Alternatively, quinoline derivatives of the formula (III) can also beprepared analogously to the processes described in Organic Reactions(Hoboken, N.J., United States), 28, 1982 and Journal of OrganicChemistry 2016, 81, 57-65 via a ring expansion of the correspondingindole derivatives.

Examples of suitable bases are, for example, lithium hydroxide or sodiumhydroxide. Solvents used may be polar aprotic and protic solvents andmixtures of these, for example ethanol, tetrahydrofuran or water.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Process G-1

Carboxylic acids of the formula (III′-A) are either commerciallyavailable or can be prepared by known methods, for example frombenzylamines or hetarylmethanamines in analogy to the processesdescribed in Tetrahedron, 40 (1984), 311-314, Monatshefte für Chemie,139 (2008), 673-684, Synlett, 3 (2006), 379-382; Indian Journal ofChemistry, Section B: Organic Chemistry Including Medicinal Chemistry,22B (1983), 178-179; Journal of Organic Chemistry, 55 (1990), 2838-2842;Heterocycles, 60 (2003), 953-957; Chemical Communications, 2 (2002),180-181, WO2015/071178, Bioorganic & Medicinal Chemistry Letters, 24(2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003/010146.

The radicals R², R³, R⁷, Aa, Ab, Ac, Ad and Ae have the definitionsdescribed above. E is hydrogen or halogen and X¹ is halogen. Y² ismethyl, C(O)OR⁸ or cyano. R⁸ is hydrogen or C₁-C₆-alkyl.

Step a)

The compounds of the formula (XXIV) can be synthesized in analogy to theprocesses described in Tetrahedron, 40 (1984), 311-314 or Monatsheftefür Chemie, 139 (2008), 673-684 via a condensation of benzylamines orhetarylmethanamines of the formula (XXIII) with the correspondingcarbonyl compounds under acidic or basic conditions.

The compounds of the formula (XXIII) are either commercially availableor can be prepared by known methods, for example in analogy to themethods described in WO1997/41846; US2011/0105753; Journal of MedicinalChemistry, 46 (2003), 461-473; WO2010/024430; WO2005/111003; Journal ofHeterocyclic Chemistry, 23 (1986), 989-990.

Step b)

Compounds of the formula (XXV) can be prepared by known methods, forexample via a hydrolysis of compounds of the formula (XXIV) (ifY²═C(O)OR⁸ or cyano) under acidic, basic or thermal conditions.

Compounds of the formula (XXV) can be prepared in analogy to theprocesses described in Synlett, 3 (2006), 379-382; Indian Journal ofChemistry, Section B: Organic Chemistry Including Medicinal Chemistry,22B (1983), 178-179; Journal of Organic Chemistry, 55 (1990), 2838-2842;Heterocycles, 60 (2003), 953-957; Chemical Communications, 2 (2002),180-181 and WO2015/071178, via a benzylic oxidation from compounds ofthe formula (XXIV) (if Y²=methyl).

Step c)

Compounds of the formula (III′-A) can be prepared by known methods fromcompounds of the formula (XXV) via a halogenation. This can be effected,for example, via a directed ortho-lithiation, followed by capture of thecarbanion with a suitable electrophilic halogenating reagent oralternatively via a carboxylic acid derivative-directed halogenation inanalogy to the processes described in Bioorganic & Medicinal ChemistryLetters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 andWO2003/010146 (cf. Process F, step c).

Process G-2

Step a)

Compounds of the formula (XXIX) can be prepared by known methods fromcompounds of the formula (XXVIII) via a halogenation. This can beeffected, for example, via a directed ortho-lithiation, followed bycapture of the carbanion with a suitable electrophilic halogenatingreagent or alternatively via an electrophilic aromatic halogenation inanalogy to the processes described in Bioorganic & Medicinal ChemistryLetters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 andWO2003/010146 (cf. Process F-1, step c). Compounds of the formula(XXVIII) are commercially available or can be synthesized via anesterification from compounds of the formula (XXV).

Step b)

The compounds of the formula (III″) can be synthesized in analogy to theprocesses described in Synthesis 1987, 6, 586-587, Tetrahedron Letters2006, 47, 565-567 or ChemMedChem 2010, 5, 65-78 via a hydrolysis fromthe compounds of the formula (XXIX).

Examples of suitable bases are, for example, lithium hydroxide or sodiumhydroxide. Solvents used may be polar aprotic and protic solvents andmixtures of these, for example ethanol, tetrahydrofuran or water.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Process H

Carboxylic acids of the formula (III′-B) are either commerciallyavailable or can be prepared by known methods, for example fromhaloarylcarboxylic acids or the corresponding haloheteroarylcarboxylicacids in analogy to the processes described in Science of Synthesis, 16(2004), 1109-1153 and Journal of Medicinal Chemistry, 58 (2015),480-511.

The radicals R², R³, Ab, Ac, Ad and Ae have the definitions describedabove. X¹ is halogen. R⁹ is C₁-C₆-alkyl.

Step a)

The compounds of the formula (XXVII) can be synthesized in analogy tothe processes described in WO2004/039802 oder Science of Synthesis, 16(2004), 1109-1153 via an acetylation of an alkyl 2-diazoacetate with acompound of the formula (XXVI), followed by an N-arylation which leadsto the fused bicyclic system.

The compounds of the formula (XXVI) are either commercially available orcan be prepared by known methods, for example in analogy to theprocesses described in Synthesis, 47 (2015), 1861-1868; Justus LiebigsAnnalen der Chemie, (1893), 54-57; Journal of the American ChemicalSociety, 65 (1943), 476-477; Bioorganic & Medicinal Chemistry Letters,24 (2014), 4236-4238; Organic Letters, 10 (2008), 2701-2704; Journal dePharmacie de Belgique, 22 (1967), 257-263; Journal of Organic Chemistry,60 (1995), 292-296; Bioorganic & Medicinal Chemistry Letters, 23 (2013),1846-1852; JP2012/092060; EU1983/92117; Tetrahedron, 71 (2015), 252-258.

Step b)

Compounds of the formula (III′^(-B)) can be prepared by known methods,for example via chlorination with phosphorus oxychloride of compounds ofthe formula (XXVII), as described in Journal of Medicinal Chemistry, 58(2015), 480-511.

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) or the formula (I′) are allowed toact on animal pests and/or their habitat. The control of the animalpests is preferably conducted in agriculture and forestry, and inmaterial protection. This preferably excludes methods for surgical ortherapeutic treatment of the human or animal body and diagnostic methodscarried out on the human or animal body.

The invention further relates to the use of the compounds of the formula(I) or the formula (I′) as pesticides, especially crop protectionagents.

In the context of the present application, the term “pesticide” in eachcase also always encompasses the term “crop protection agent”.

The compounds of the formula (I) or the formula (I′), given good planttolerance, favourable homeotherm toxicity and good environmentalcompatibility, are suitable for protecting plants and plant organsagainst biotic and abiotic stress factors, for increasing harvestyields, for improving the quality of the harvested material and forcontrolling animal pests, especially insects, arachnids, helminths,especially nematodes and molluscs, which are encountered in agriculture,in horticulture, in animal husbandry, in aquatic cultures, in forests,in gardens and leisure facilities, in the protection of stored productsand of materials, and in the hygiene sector.

In the context of the present patent application, the term “hygiene”should be understood to mean any and all measures, provisions andprocedures which have the aim of preventing diseases, especiallyinfection diseases, and which serve to protect the health of humans andanimals and/or protect the environment and/or maintain cleanliness.According to the invention, this especially includes measures forcleaning, disinfection and sterilization, for example of textiles orhard surfaces, especially surfaces made of glass, wood, cement,porcelain, ceramic, plastic or else metal(s), in order to ensure thatthese are free of hygiene pests and/or their secretions. The scope ofprotection of the invention in this regard preferably excludes surgicalor therapeutic treatment procedures to be applied to the human body orthe bodies of animals, and diagnostic procedures which are conducted onthe human body or the bodies of animals.

The term “hygiene sector” covers all areas, technical fields andindustrial applications in which these hygiene measures, provisions andprocedures are important, for example with regard to hygiene inkitchens, bakeries, airports, bathrooms, swimming pools, departmentstores, hotels, hospitals, stalls, animal keeping, etc.

The term “hygiene pest” should therefore be understood to mean one ormore animal pests whose presence in the hygiene sector is problematic,especially for reasons of health. A main aim is therefore that ofavoiding, or limiting to a minimum degree, the presence of hygiene pestsand/or the exposure to these in the hygiene sector. This can especiallybe achieved through the use of a pesticide which can be used both forprevention of infestation and for prevention of an existing infestation.It is also possible to use formulations which prevent or reduce exposureto pests. Hygiene pests include, for example, the organisms mentionedbelow.

The term “hygiene protection” thus covers all acts by which thesehygiene measures, provisions and procedures are maintained and/orimproved.

The compounds of the formula (I) or the formula (I′) can preferably beused as pesticides. They are active against normally sensitive andresistant species and also against all or some stages of development.The abovementioned pests include:

pests from the phylum of the Arthropoda, especially from the class ofthe Arachnida, for example Acarus spp., e.g. Acarus siro, Aceria kuko,Aceria sheldoni, Aculops spp., Aculus spp., e.g. Aculus fockeui, Aculusschlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp.,Boophilus spp., Brevipalpus spp., e.g. Brevipalpus phoenicis, Bryobiagraminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp.,Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoidesfarinae, Dermacentor spp., Eotetranychus spp., e.g. Eotetranychushicoriae, Epitrimerus pyri, Eutetranychus spp., e.g. Eutetranychusbanksi, Eriophyes spp., e.g. Eriophyes pyri, Glycyphagus domesticus,Halotydeus destructor, Hemitarsonemus spp., e.g. Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., e.g. Oligonychus coffeae, Oligonychus coniferarum,Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus,Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi,Ornithodorus spp., Ornithonyssus spp., Panonychus spp., e.g. Panonychuscitri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi),Phyllocoptruta oleivora, Platytetranychus multidigituli,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemusspp., Steneotarsonemus spinki, Tarsonemus spp., e.g. Tarsonemusconfusus, Tarsonemus pallidus, Tetranychus spp., e.g. Tetranychuscanadensis, Tetranychus cinnabarinus, Tetranychus turkestani,Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici;

from the class of the Chilopoda, e.g. Geophilus spp., Scutigera spp.;

from the order or the class of the Collembola, e.g. Onychiurus armatus;Sminthurus viridis;

from the class of the Diplopoda, e.g. Blaniulus guttulatus;

from the class of the Insecta, for example from the order of theBlattodea, e.g. Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Loboptera decipiens, Neostylopygarhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., e.g.Periplaneta americana, Periplaneta australasiae, Pycnoscelussurinamensis, Supella longipalpa;

from the order of the Coleoptera for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelasticaalni, Agriotes spp., e.g. Agriotes linneatus, Agriotes mancus,Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum,Anoplophora spp., Anthonomus spp., e.g. Anthonomus grandis, Anthrenusspp., Apion spp., Apogonia spp., Atomaria spp., e.g. Atomaria linearis,Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp.,e.g. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotomatrifurcata, Ceutorrhynchus spp., e.g. Ceutorrhynchus assimilis,Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., e.g.Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa,Cleonus mendicus, Conoderus spp., Cosmopolites spp., e.g. Cosmopolitessordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., e.g.Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi,Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi,Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturusadspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp.,e.g. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctatahowardi, Diabrotica undecimpunctata undecimpunctata, Diabroticavirgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp.,Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp.,e.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., e.g.Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrixsubcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides,Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyxspp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomecessquamosus, Hypothenemus spp., e.g. Hypothenemus hampei, Hypothenemusobscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasiodermaserricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsadecemlineata, Leucoptera spp., e.g. Leucoptera coffeella, Lissorhoptrusoryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp.,Luperomorpha xanthodera, Lyctus spp., Megascelis spp., Melanotus spp.,e.g. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp.,e.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactusxanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus,Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae,Otiorhynchus spp., e.g. Otiorhynchus cribricollis, Otiorhynchusligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus,Otiorhynchus sulcatus, Oulema spp., e.g. Oulema melanopus, Oulemaoryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Phyllophaga helleri, Phyllotreta spp., e.g. Phyllotreta armoraciae,Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popilliajaponica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp.,e.g. Psylliodes affinis, Psylliodes chrysocephala, Psylliodespunctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica,Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum,Sinoxylon perforans, Sitophilus spp., e.g. Sitophilus granarius,Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorusspp., Stegobium paniceum, Sternechus spp., e.g. Sternechus paludatus,Symphyletes spp., Tanymecus spp., e.g. Tanymecus dilaticollis, Tanymecusindicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioidesmauretanicus, Tribolium spp., e.g. Tribolium audax, Tribolium castaneum,Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp.,Zabrus spp., e.g. Zabrus tenebrioides;

from the order of the Dermaptera, for example Anisolabis maritime,Forficula auricularia, Labidura riparia;

from the order of the Diptera, for example Aedes spp., e.g. Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,e.g. Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., e.g. Anopheles quadrimaculatus, Anopheles gambiae,Asphondylia spp., Bactrocera spp., e.g. Bactrocera cucurbitae,Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphoraerythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp.,Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp.,Contarinia spp., e.g. Contarinia johnsoni, Contarinia nasturtii,Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola,Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris,Culex spp., e.g. Culex pipiens, Culex quinquefasciatus, Culicoides spp.,Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., e.g.Dasineura brassicae, Delia spp., e.g. Delia antiqua, Delia coarctata,Delia florilega, Delia platura, Delia radicum, Dermatobia hominis,Drosophila spp., e.g. Drosphila melanogaster, Drosophila suzukii,Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp.,Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola,Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., e.g.Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Luciliaspp., e.g. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp.,e.g. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinellafrit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya oderPegomyia spp., e.g. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora,Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platypareapoeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., e.g.Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletisindifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp.,Simulium spp., e.g. Simulium meridionale, Stomoxys spp., Tabanus spp.,Tetanops spp., Tipula spp., e.g. Tipula paludosa, Tipula simplex,Toxotrypana curvicauda;

from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., e.g. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobusbarodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrascaspp., e.g. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui,Aonidiella spp., e.g. Aonidiella aurantii, Aonidiella citrina,Aonidiella inornata, Aphanostigma pini, Aphis spp., e.g. Aphiscitricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines,Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni,Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphisviburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp.,Aspidiotus spp., e.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani,Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae,Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae,Cacopsylla spp., e.g. Cacopsylla pyricola, Calligypona marginata,Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera,Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspistegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola,Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila,Coccomytilus halli, Coccus spp., e.g. Coccus hesperidum, Coccuslongulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis,Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodeschittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp.,Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., e.g.Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccusspp., Empoasca spp., e.g. Empoasca abrupta, Empoasca fabae, Empoascamaligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., e.g.Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneuraspp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisiaspp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspisspp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodiscacoagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., e.g.Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., e.g. Lecanium corni (=Parthenolecaniumcorni), Lepidosaphes spp., e.g. Lepidosaphes ulmi, Lipaphis erysimi,Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., e.g.Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae,Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiellaspp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., e.g. Myzus ascalonicus, Myzus cerasi,Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae,Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., e.g.Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra,Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxyachinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., e.g.Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., e.g. Pemphigusbursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp.,Phenacoccus spp., e.g. Phenacoccus madeirensis, Phloeomyzus passerinii,Phorodon humuli, Phylloxera spp., e.g. Phylloxera devastatrix,Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., e.g.Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis,Pseudaulacaspis pentagona, Pseudococcus spp., e.g. Pseudococcuscalceolariae, Pseudococcus comstocki, Pseudococcus longispinus,Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psyllaspp., e.g. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp.,Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., e.g.Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis,Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp.,Rhopalosiphum spp., e.g. Rhopalosiphum maidis, Rhopalosiphumoxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetiaspp., e.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta,Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidusarticulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatellafurcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae,Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae,Tomaspis spp., Toxoptera spp., e.g. Toxoptera aurantii, Toxopteracitricidus, Trialeurodes vaporariorum, Trioza spp., e.g. Triozadiospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;

from the suborder of the Heteroptera, for example Aelia spp., Anasatristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp.,Campylomma livida, Cavelerius spp., Cimex spp., e.g. Cimex adjunctus,Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp.,Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocorishewetti, Dysdercus spp., Euschistus spp., e.g. Euschistus heros,Euschistus servus, Euschistus tristigmus, Euschistus variolarius,Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp.,Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis,Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., e.g.Lygocoris pabulinus, Lygus spp., e.g. Lygus elisus, Lygus hesperus,Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae,Monalonion atratum, Nezara spp., e.g. Nezara viridula, Nysius spp.,Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., e.g.Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp.,Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp.,Stephanitis nashi, Tibraca spp., Triatoma spp.;

from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., e.g. Athalia rosae, Atta spp., Camponotus spp., Dolichovespulaspp., Diprion spp., e.g. Diprion similis, Hoplocampa spp., e.g.Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema(Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp.,Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta,Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., e.g.Vespa crabro, Wasmannia auropunctata, Xeris spp.;

from the order of the Isopoda, for example Armadillidium vulgare,Oniscus asellus, Porcellio scaber;

from the order of the Isoptera, for example Coptotermes spp., e.g.Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp.,Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermesspp., Odontotermes spp., Porotermes spp., Reticulitermes spp., e.g.Reticulitermes flavipes, Reticulitermes hesperus;

from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., e.g. Adoxophyes orana, Aedialeucomelas, Agrotis spp., e.g. Agrotis segetum, Agrotis ipsilon, Alabamaspp., e.g. Alabama argillacea, Amyelois transitella, Anarsia spp.,Anticarsia spp., e.g. Anticarsia gemmatalis, Argyroploce spp.,Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara,Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoeciaspp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella,Carposina niponensis, Cheimatobia brumata, Chilo spp., e.g. Chiloplejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp.,Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp.,Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp.,Conotrachelus spp., Copitarsia spp., Cydia spp., e.g. Cydia nigricana,Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp.,Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpuslignosellus, Eldana saccharina, Ephestia spp., e.g. Ephestia elutella,Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp.,Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp.,Eupoecilia ambiguella, Euproctis spp., e.g. Euproctis chrysorrhoea,Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp.,Grapholitha spp., e.g. Grapholita molesta, Grapholita prunivora,Hedylepta spp., Helicoverpa spp., e.g. Helicoverpa armigera, Helicoverpazea, Heliothis spp., e.g. Heliothis virescens Hofmannophilapseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella,Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresiamolesta, Leucinodes orbonalis, Leucoptera spp., e.g. Leucopteracoffeella, Lithocolletis spp., e.g. Lithocolletis blancardella,Lithophane antennata, Lobesia spp., e.g. Lobesia botrana, Loxagrotisalbicosta, Lymantria spp., e.g. Lymantria dispar, Lyonetia spp., e.g.Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestrabrassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimnaseparata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisaspp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., e.g.Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp.,e.g. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp.,e.g. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycterspp., e.g. Phyllonorycter blancardella, Phyllonorycter crataegella,Pieris spp., e.g. Pieris rapae, Platynota stultana, Plodiainterpunctella, Plusia spp., Plutella xylostella (=Plutellamaculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletiaspp., e.g. Pseudaletia unipuncta, Pseudoplusia includens, Pyraustanubilalis, Rachiplusia nu, Schoenobius spp., e.g. Schoenobiusbipunctifer, Scirpophaga spp., e.g. Scirpophaga innotata, Scotiasegetum, Sesamia spp., e.g. Sesamia inferens, Sparganothis spp.,Spodoptera spp., e.g. Spodoptera eradiana, Spodoptera exigua, Spodopterafrugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp.,Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora,Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tineapellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella,Trichoplusia spp., e.g. Trichoplusia ni, Tryporyza incertulas, Tutaabsoluta, Virachola spp.;

from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., e.g. Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., e.g. Locusta migratoria,Melanoplus spp., e.g. Melanoplus devastator, Paratlanticus ussuriensis,Schistocerca gregaria;

from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;

from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;

from the order of the Siphonaptera, for example Ceratophyllus spp.,Ctenocephalides spp., e.g. Ctenocephalides canis, Ctenocephalides felis,Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri,Enneothrips flavens, Frankliniella spp., e.g. Frankliniella fusca,Frankliniella occidentalis, Frankliniella schultzei, Frankliniellatritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothripsspp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp.,Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi,Thrips spp., e.g. Thrips palmi, Thrips tabaci;

from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

from the class of the Symphyla, for example Scutigerella spp., e.g.Scutigerella immaculata;

pests from the phylum of the Mollusca, for example from the class of theBivalvia, e.g. Dreissena spp.;

and also from the class of the Gastropoda, for example Anion spp., e.g.Anion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., e.g.Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomaceaspp., Succinea spp.;

plant pests from the phylum of the Nematoda, i.e. plant-parasiticnematodes, in particular Aglenchus spp., e.g. Aglenchus agricola,Anguina spp., e.g. Anguina tritici, Aphelenchoides spp., e.g.Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp.,e.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimusnortoni, Bursaphelenchus spp., e.g. Bursaphelenchus cocophilus,Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp.,e.g. Cacopaurus pestis, Criconemella spp., e.g. Criconemella curvata,Criconemella onoensis, Criconemella ornata, Criconemella rusium,Criconemella xenoplax (=Mesocriconema xenoplax), Criconemoides spp.,e.g. Criconemoides ferniae, Criconemoides onoense, Criconemoidesornatum, Ditylenchus spp., e.g. Ditylenchus dipsaci, Dolichodorus spp.,Globodera spp., e.g. Globodera pallida, Globodera rostochiensis,Helicotylenchus spp., e.g. Helicotylenchus dihystera, Hemicriconemoidesspp., Hemicycliophora spp., Heterodera spp., e.g. Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hirschmaniella spp.,Hoplolaimus spp., Longidorus spp., e.g. Longidorus africanus,Meloidogyne spp., e.g. Meloidogyne chitwoodi, Meloidogyne fallax,Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp.,Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp.,Paratrichodorus spp., e.g. Paratrichodorus minor, Paratylenchus spp.,Pratylenchus spp., e.g. Pratylenchus penetrans, Pseudohalenchus spp.,Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp.,e.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp.,Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp.,e.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp.,e.g. Tylenchorhynchus annulatus, Tylenchulus spp., e.g. Tylenchulussemipenetrans, Xiphinema spp., e.g. Xiphinema index.

The compounds of the formula (I) or the formula (I′) can, as the casemay be, at certain concentrations or application rates, also be used asherbicides, safeners, growth regulators or agents to improve plantproperties, as microbicides or gametocides, for example as fungicides,antimycotics, bactericides, virucides (including agents against viroids)or as agents against MLO (mycoplasma-like organisms) and RLO(rickettsia-like organisms). They can, as the case may be, also be usedas intermediates or precursors for the synthesis of other activeingredients.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I) or theformula (I′). Optionally, the use forms comprise further pesticidesand/or adjuvants which improve action, such as penetrants, e.g.vegetable oils, for example rapeseed oil, sunflower oil, mineral oils,for example paraffin oils, alkyl esters of vegetable fatty acids, forexample rapeseed oil methyl ester or soya oil methyl ester, or alkanolalkoxylates and/or spreaders, for example alkylsiloxanes and/or salts,for example organic or inorganic ammonium or phosphonium salts, forexample ammonium sulphate or diammonium hydrogenphosphate and/orretention promoters, for example dioctyl sulphosuccinate orhydroxypropylguar polymers and/or humectants, for example glyceroland/or fertilizers, for example ammonium-, potassium- orphosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further formulation typesare described, for example, by Crop Life International and in PesticideSpecifications, Manual on development and use of FAO and WHOspecifications for pesticides, FAO Plant Production and ProtectionPapers—173, prepared by the FAO/WHO Joint Meeting on PesticideSpecifications, 2004, ISBN: 9251048576. The formulations, in addition toone or more compounds of the formula (I) or the formula (I′), optionallycomprise further active agrochemical ingredients.

Preference is given to formulations or use forms comprising auxiliaries,for example extenders, solvents, spontaneity promoters, carriers,emulsifiers, dispersants, frost protection agents, biocides, thickenersand/or further auxiliaries, for example adjuvants. An adjuvant in thiscontext is a component which enhances the biological effect of theformulation, without the component itself having any biological effect.Examples of adjuvants are agents which promote retention, spreading,attachment to the leaf surface or penetration.

These formulations are prepared in a known way, for example by mixingthe compounds of the formula (I) or the formula (I′) with auxiliaries,for example extenders, solvents and/or solid carriers and/or otherauxiliaries, for example surfactants. The formulations are producedeither in suitable facilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I) orthe formula (I′), or to the use forms prepared from these formulations(for example ready-to-use pesticides such as spray liquors or seeddressing products).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the simple and substituted amines, amides,lactams (such as N-alkylpyrrolidones) and lactones, the sulphones andsulphoxides (such as dimethyl sulphoxide).

If the extender utilized is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Useful liquid solventsare essentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example mineral oilfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and alsowater.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, for example xylene, tolueneor alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons,for example chlorobenzene, chloroethylene or methylene chloride,aliphatic hydrocarbons, for example cyclohexane, paraffins, petroleumfractions, mineral and vegetable oils, alcohols, for example methanol,ethanol, isopropanol, butanol or glycol and their ethers and esters,ketones, for example acetone, methyl ethyl ketone, methyl isobutylketone or cyclohexanone, strongly polar solvents, for example dimethylsulphoxide, and water.

In principle, it is possible to use all suitable carriers. Usefulcarriers especially include, for example, ammonium salts and natural,finely ground rocks, such as kaolins, aluminas, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and synthetic,finely ground rocks, such as highly disperse silica, aluminium oxide andnatural or synthetic silicates, resins, waxes and/or solid fertilizers.It is likewise possible to use mixtures of such carriers. Usefulcarriers for granules include: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite, dolomite, andsynthetic granules of inorganic and organic flours, and also granules oforganic material such as sawdust, paper, coconut shells, maize cobs andtobacco stalks.

It is also possible to use liquefied gaseous extenders or solvents.Especially suitable extenders or carriers are those which are gaseous atstandard temperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents having ionic or nonionic properties or mixtures of thesesurface-active substances are salts of polyacrylic acid, salts oflignosulphonic acid, salts of phenolsulphonic acid ornaphthalenesulphonic acid, polycondensates of ethylene oxide with fattyalcohols or with fatty acids or with fatty amines, with substitutedphenols (preferably alkylphenols or arylphenols), salts ofsulphosuccinic esters, taurine derivatives (preferably alkyl taurates),phosphoric esters of polyethoxylated alcohols or phenols, fatty acidesters of polyols, and derivatives of the compounds containingsulphates, sulphonates and phosphates, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates, proteinhydrolysates, lignosulphite waste liquors and methylcellulose. Thepresence of a surfactant is advantageous if one of the compounds of theformula (I) or the formula (I′) and/or one of the inert carriers isinsoluble in water and when the application is effected in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom include dyes such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organic dyessuch as alizarin dyes, azo dyes and metal phthalocyanine dyes, andnutrients and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Additional components which may be present are stabilizers, such as coldstabilizers, preservatives, antioxidants, light stabilizers, or otheragents which improve chemical and/or physical stability. Foam generatorsor antifoams may also be present.

In addition, the formulations and the use forms derived therefrom mayalso comprise, as additional auxiliaries, stickers such ascarboxymethylcellulose and natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further auxiliaries may bemineral and vegetable oils.

It is possible if appropriate for still further auxiliaries to bepresent in the formulations and the use forms derived therefrom.Examples of such additives are fragrances, protective colloids, binders,adhesives, thickeners, thixotropic agents, penetrants, retentionpromoters, stabilizers, sequestrants, complexing agents, humectants,spreaders. In general, the compounds of the formula (I) or the formula(I′) can be combined with any solid or liquid additive commonly used forformulation purposes.

Useful retention promoters include all those substances which reducedynamic surface tension, for example dioctyl sulphosuccinate, orincrease viscoelasticity, for example hydroxypropylguar polymers.

Suitable penetrants in the present context are all those substanceswhich are usually used for improving the penetration of activeagrochemical ingredients into plants. Penetrants are defined in thiscontext by their ability to penetrate from the (generally aqueous)application liquor and/or from the spray coating into the cuticle of theplant and hence increase the mobility of the active ingredients in thecuticle. The method described in the literature (Baur et al., 1997,Pesticide Science 51, 131-152) can be used for determining thisproperty. Examples include alcohol alkoxylates such as coconut fattyethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters, forexample rapeseed oil methyl ester or soya oil methyl ester, fatty aminealkoxylates, for example tallowamine ethoxylate (15), or ammonium and/orphosphonium salts, for example ammonium sulphate or diammoniumhydrogenphosphate.

The formulations preferably comprise between 0.00000001% and 98% byweight of the compound of the formula (I) or the formula (I′), morepreferably between 0.01% and 95% by weight of the compound of theformula (I) or the formula (I′), most preferably between 0.5% and 90% byweight of the compound of the formula (I) or the formula (I′), based onthe weight of the formulation.

The content of the compound of the formula (I) or the formula (I′) inthe use forms prepared from the formulations (in particular pesticides)may vary within wide ranges. The concentration of the compound of theformula (I) or the formula (I′) in the use forms may typically bebetween 0.00000001% and 95% by weight of the compound of the formula (I)or the formula (I′), preferably between 0.00001% and 1% by weight, basedon the weight of the use form. Application is accomplished in acustomary manner appropriate for the use forms.

Mixtures

The compounds of the formula (I) or the formula (I′) can also be used ina mixture with one or more suitable fungicides, bactericides,acaricides, molluscicides, nematicides, insecticides, microbiologicalagents, beneficial organisms, herbicides, fertilizers, bird repellents,phytotonics, sterilants, safeners, semiochemicals and/or plant growthregulators, in order thus, for example, to broaden the spectrum ofaction, prolong the period of action, enhance the rate of action,prevent repellency or prevent evolution of resistance. In addition,active ingredient combinations of this kind can improve plant growthand/or tolerance to abiotic factors, for example high or lowtemperatures, to drought or to elevated water content or soil salinity.It is also possible to improve flowering and fruiting performance,optimize germination capacity and root development, facilitateharvesting and improve yields, influence maturation, improve the qualityand/or the nutritional value of the harvested products, prolong storagelife and/or improve the processability of the harvested products.

In addition, the compounds of the formula (I) or the formula (I′) may bepresent in a mixture with other active ingredients or semiochemicalssuch as attractants and/or bird repellents and/or plant activatorsand/or growth regulators and/or fertilizers. Likewise, the compounds ofthe formula (I) or the formula (I′) can be used to improve plantproperties, for example growth, yield and quality of the harvestedmaterial.

In a particular embodiment according to the invention, the compounds ofthe formula (I) or the formula (I′) are present in formulations or inthe use forms prepared from these formulations in a mixture with furthercompounds, preferably those as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case. All the mixing components mentioned, as the casemay be, may also form salts with suitable bases or acids if they arecapable of doing so on the basis of their functional groups.

Insecticides/Acaricides/Nematicides

The active ingredients specified here with their common names are knownand are described for example in “The Pesticide Manual”, 16th ed.,British Crop Protection Council 2012, or can be searched for on theInternet (e.g. http://www.alanwood.net/pesticides). The classificationis based on the IRAC Mode of Action Classification Scheme applicable atthe time of filing of this patent application.

(1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g.alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim,butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb,fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl,metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox,triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, e.g.acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos,chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl,coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos,propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos,sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos,thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel blockers, for examplecyclodiene-organochlorines, e.g. chlordane and endosulfan orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

(3) Sodium channel modulators, for example pyrethroids, e.g.acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin,bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer,bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin[(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R) isomer],esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate,flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin,momfluorothrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin,pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin,tetramethrin, tetramethrin [(1R) isomer)], tralomethrin andtransfluthrin or DDT or methoxychlor.

(4) Nicotinergic acetylcholine receptor (nAChR) competitive modulators,for example neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulfoxaflor or flupyradifurone.

(5) Nicotinergic acetylcholine receptor (nAChR) allosteric modulators,for example spinosyns, e.g. spinetoram and spinosad.

(6) Glutamate-gated chloride channel (GluCl) allosteric modulators, forexample avermectins/milbemycins, e.g. abamectin, emamectin benzoate,lepimectin and milbemectin.

(7) Juvenile hormone mimetics, for example, juvenile hormone analogues,e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Miscellaneous non-specific (multisite) inhibitors, for example alkylhalides, e.g. methyl bromide and other alkyl halides; or chloropicrin orsulphuryl fluoride or borax or tartar emetic or methyl isocyanategenerator, e.g. diazomet and metam.

(9) Chordotonal organ modulators, e.g. pymetrozine or flonicamide.

(10) Mite growth inhibitors, for example clofentezine, hexythiazox anddiflovidazin or etoxazole.

(11) Microbial disruptors of the insect midgut membrane, for exampleBacillus thuringiensis subspecies israelensis, Bacillus sphaericus,Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensissubspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis andB.t. plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, VIP3A,mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/35Ab1.

(12) Inhibitors of mitochondrial ATP synthase, such as ATP disruptors,for example diafenthiuron or organotin compounds, e.g. azocyclotin,cyhexatin and fenbutatin oxide or propargite or tetradifon.

(13) Uncouplers of oxidative phosphorylation via disruption of theproton gradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinergic acetylcholine receptor channel blockers, for examplebensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, for examplebistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

(17) Moulting disruptors (especially in the case of Diptera), forexample cyromazine.

(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists, for example amitraz.

(20) Mitochondrial complex III electron transport inhibitors, forexample hydramethylnon or acequinocyl or fluacrypyrim.

(21) Mitochondrial complex I electron transport inhibitors, for exampleMETI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers, for example indoxacarbor metaflumizone.

(23) Inhibitors of acetyl CoA carboxylase, for example tetronic andtetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.

(24) Mitochondrial complex IV electron transport inhibitors, for examplephosphines, e.g. aluminium phosphide, calcium phosphide, phosphine andzinc phosphide, or cyanides, calcium cyanide, potassium cyanide andsodium cyanide.

(25) Mitochondrial complex II electron transport inhibitors, for examplebeta-keto nitrile derivatives, e.g. cyenopyrafen and cyflumetofen andcarboxanilide, for example pyflubumide.

(28) Ryanodine receptor modulators, for example diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide,

further active ingredients, for example afidopyropen, afoxolaner,azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide,bromopropylate, chinomethionat, chloroprallethrin, cryolite,cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol,epsilon metofluthrin, epsilon momfluthrin, flometoquin,fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin,flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide,fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappabifenthrin, kappa tefluthrin, lotilaner, meperfluthrin, paichongding,pyridalyl, pyrifluquinazon, pyriminostrobin, spirobudiclofen,tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole,tioxazafen, thiofluoximate, triflumezopyrim and iodomethane;additionally preparations based on Bacillus firmus (I-1582, BioNeem,Votivo), and the following compounds:1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635) (CAS 885026-50-6),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4′-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO2003/106457) (CAS 637360-23-7),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494) (CAS 872999-66-1),3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO 2010052161) (CAS 1225292-17-0),3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethylcarbonate (known from EP 2647626) (CAS-1440516-42-6),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160) (CAS 792914-58-0), PF1364 (known fromJP2010/018586) (CAS Reg. No. 1204776-60-2),N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(known from WO2012/029672) (CAS 1363400-41-2),(3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one(known from WO2013/144213) (CAS 1461743-15-6),N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide(known from WO2010/051926) (CAS 1226889-14-0),5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide(known from CN103232431) (CAS 1449220-44-3),4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)benzamideand4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide(known from WO 2013/050317 A1) (CAS 1332628-83-7),N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulphinyl]propanamide,(+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulphinyl]propanamideand(−)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulphinyl]propanamide(known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1)(CAS 1477923-37-7),5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulphinyl]-1H-pyrazole-3-carbonitrile(known from CN 101337937 A) (CAS 1105672-77-2),3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide,(Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9);N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO 2012/034403 A1) (CAS 1268277-22-0),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(known from WO 2011/085575 A1) (CAS 1233882-22-8),4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide(known from CN 101715774 A) (CAS 1232543-85-9); cyclopropanecarboxylicacid 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylester (known from CN 103524422 A) (CAS 1542271-46-4);(4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylicacid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2);6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose(known from US 2014/0275503 A1) (CAS 1181213-14-8);8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 1253850-56-4),(8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 933798-27-7),(8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8) andN-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide(known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9).

Fungicides

The active ingredients specified here by their “common names” are knownand are described, for example, in the “Pesticide Manual” (16th ed.,British Crop Protection Council) or can be searched for on the Internet(for example: http://www.alanwood.net/pesticides).

All the mixing components mentioned in classes (1) to (15), as the casemay be, may form salts with suitable bases or acids if they are capableof doing so on the basis of their functional groups. All the fungicidalmixing components of classes (1) to (15) mentioned, as the case may be,may include tautomeric forms.

1) Ergosterol biosynthesis inhibitors, for example (1.001)cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004)fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007)fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010)imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013)metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016)prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019)pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022)tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025)triticonazole, (1.026)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol(1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.032)(2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.033)(2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.037)1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.038)1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.039)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl}methyl]-1H-1,2,4-triazol-5-ylthiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl}methyl]-1H-1,2,4-triazol-5-ylthiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl}methyl]-1H-1,2,4-triazol-5-ylthiocyanate, (1.042)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.044)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.046)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.047)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.048)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.049)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.050)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.051)2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.052)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.054)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol,(1.055)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.056)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl}methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl}methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.058)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl}methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.059)5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.060)5-(allylsulphanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl}methyl]-1H-1,2,4-triazole,(1.061)5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl}methyl]-1H-1,2,4-triazole,(1.062)5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl}methyl]-1H-1,2,4-triazole,(1.063)N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.064)N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.065)N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.066)N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.067)N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulphanyl]phenoxyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.068)N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.069)N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.070)N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.071)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(1.072)N′-(4-{[3-(difluoromethoxy)phenyl]sulphanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.073)N′-(4-{3-[(difluoromethyl)sulphanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.074)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(1.075)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(1.076)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.077)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.078)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.079)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.080)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide.

2) Inhibitors of the respiratory chain in complex I or II, for example(2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004)carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad,(2.008) furametpyr, (2.009) isofetamid, (2.010) isopyrazam(anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimericenantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate1RS,4SR,9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate1RS,4SR,9RS and the anti-epimeric racemate 1RS,4SR,9SR), (2.014)isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam(syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019)pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.023)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.024)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.025)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.026)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(2.027)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.028)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.029)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.030)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.031)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.032)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.033)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine,(2.034)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.035)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.036)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.037)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.038)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.039)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.041)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.042)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.044)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.045)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(2.046)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.047)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.048)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide,(2.049)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.050)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.051)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.052)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.053)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.054)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.055)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.056)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.

3) Inhibitors of the respiratory chain in complex III, for example(3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004)coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007)dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadon, (3.010)fenamidon, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013)kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016)picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019)pyraoxystrobin, (3.020) trifloxystrobin (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,(3.022)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.024)(2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.025)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (3.026)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.027)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,(3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide.

4) Mitosis and cell division inhibitors, for example (4.001)carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004)fluopicolid, (4.005) pencycuron, (4.006) thiabendazole, (4.007)thiophanate-methyl, (4.008) zoxamide, (4.009)3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(4.011)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine,(4.012)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.013)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.014)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.015)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.016)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.017)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.018)4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.019)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.020)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.021)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.022)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(4.023)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.024)N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.025)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

5) Compounds having capacity for multisite activity, for example (5.001)Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004)chlorthalonil, (5.005) copper hydroxide (5.006) copper naphthenate,(5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2+)sulphate, (5.010) dithianon, (5.011) dodin, (5.012) folpet, (5.013)mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017)copper oxine, (5.018) propineb, (5.019) sulphur and sulphur preparationsincluding calcium polysulphide, (5.020) thiram, (5.021) zineb, (5.022)ziram.

6) Compounds capable of triggering host defence, for example (6.001)acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004)tiadinil.

7) Amino acid and/or protein biosynthesis inhibitors, for example(7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycinhydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil,(7.006)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

(8) ATP production inhibitors, for example (8.001) silthiofam.

9) Cell wall synthesis inhibitors, for example (9.001) benthiavalicarb,(9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005)mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(9.009)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

10) Lipid and membrane synthesis inhibitors, for example (10.001)propamocarb, (10.002) propamocarb hydrochloride, (10.003)tolclofos-methyl.

11) Melanin biosynthesis inhibitors, for example (11.001) tricyclazole,(11.002) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl,(12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004)metalaxyl-M (mefenoxam).

13) Signal transduction inhibitors, for example (13.001) fludioxonil,(13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005)quinoxyfen, (13.006) vinclozolin.

14) Compounds that can act as decouplers, for example (14.001)fluazinam, (14.002) meptyldinocap.

15) Further compounds, for example (15.001) abscisic acid, (15.002)benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone,(15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid,(15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil,(15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014)fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon,(15.017) mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021)oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024)pentachlorophenol and salts, (15.025) phosphonic acid and salts thereof,(15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone)(15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide,(15.031)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.032)1-(4-{4-[(5)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.035)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.036)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.037)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.038)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.040)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.041)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol,(15.042)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol,(15.043)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.044)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulphonate, (15.045) 2-phenylphenol and salts thereof, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.047)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.049)4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050)5-amino-1,3,4-thiadiazole-2-thiol, (15.051)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene 2-sulphonohydrazide,(15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,(15.055) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057)phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate,(15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulphate (2:1), (15.061)tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate.

Biological Pesticides as Mixing Components

The compounds of the formula (I) or the formula (I′) can be combinedwith biological pesticides.

Biological pesticides especially include bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are used or can be used as biologicalpesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, especially B. cereus strain CNCM I-1562 or Bacillus firmus,strain I-1582 (Accession number CNCM I-1582) or Bacillus pumilus,especially strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, especially strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421) Bacillus thuringiensis, especially B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai,especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Accession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are:

Beauveria bassiana, especially strain ATCC 74040, Coniothyrium minitans,especially strain CON/M/91-8 (Accession No. DSM-9660), Lecanicilliumspp., especially strain HRO LEC 12, Lecanicillium lecanii, (formerlyknown as Verticillium lecanii), especially strain KV01, Metarhiziumanisopliae, especially strain F52 (DSM3884/ATCC 90448), Metschnikowiafructicola, especially strain NRRL Y-30752, Paecilomyces fumosoroseus(now: Isaria fumosorosea), especially strain IFPC 200613, or strainApopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, especiallyP. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, especiallystrain V117b, Trichoderma atroviride, especially strain SC1 (AccessionNumber CBS 122089), Trichoderma harzianum, especially T. harzianum rifaiT39 (Accession Number CNCM I-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Examplesinclude:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especiallyBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Zaccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),pyrethrum/pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract,especially oilseed rape powder or mustard powder.

Safeners as Mixing Components

The compounds of the formula (I) or the formula (I′) can be combinedwith safeners, for example benoxacor, cloquintocet (-mexyl),cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl),fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl),mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya bean, potato, sugarbeet, sugar cane, tomatoes, bell peppers, cucumbers, melons, carrots,water melons, onions, lettuce, spinach, leeks, beans, Brassica oleracea(e.g. cabbage) and other vegetable species, cotton, tobacco, oilseedrape, and also fruit plants (the fruits being apples, pears, citrusfruits and grapes). Crop plants may be plants which can be obtained byconventional breeding and optimization methods or by biotechnologicaland genetic engineering methods or combinations of these methods,including the transgenic plants and including the plant cultivars whichare protectable or non-protectable by plant breeders' rights. Plantsshall be understood to mean all development stages such as seed,seedlings, young (immature) plants, up to and including mature plants.Plant parts shall be understood to mean all parts and organs of theplants above and below ground, such as shoot, leaf, flower and root,examples given being leaves, needles, stalks, stems, flowers, fruitbodies, fruits and seeds, and also roots, tubers and rhizomes. Plantparts also include harvested plants or harvested plant parts andvegetative and generative propagation material, for example cuttings,tubers, rhizomes, slips and seeds.

The inventive treatment of the plants and parts of plants with thecompounds of the formula (I) or the formula (I′) is effected directly orby allowing the compounds to act on the surroundings, the habitat or thestorage space thereof by the customary treatment methods, for example bydipping, spraying, evaporating, fogging, scattering, painting on,injecting, and, in the case of propagation material, especially in thecase of seeds, also by applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts in accordance with the invention. In a preferred embodiment, wildplant species and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove. Particular preference is given in accordance with the inventionto treating plants of the respective commercially customary plantcultivars or those that are in use. Plant cultivars are understood tomean plants having new properties (“traits”) and which have beenobtained by conventional breeding, by mutagenesis or by recombinant DNAtechniques. They may be cultivars, varieties, biotypes or genotypes.

Transgenic Plants, Seed Treatment and Integration Events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to levels of water or soil salinity,enhanced flowering performance, easier harvesting, accelerated ripening,higher harvest yields, higher quality and/or higher nutritional value ofthe harvested products, better storage life and/or processability of theharvested products. Further and particularly emphasized examples of suchproperties are increased resistance of the plants against animal andmicrobial pests, such as insects, arachnids, nematodes, mites, slugs andsnails, owing, for example, to toxins formed in the plants, inparticular those formed in the plants by the genetic material fromBacillus thuringiensis (for example by the genes CryIA(a), CryIA(b),CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF andalso combinations thereof), and also increased resistance of the plantsagainst phytopathogenic fungi, bacteria and/or viruses caused, forexample, by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and correspondingly expressed proteinsand toxins, and also increased tolerance of the plants to certainherbicidally active ingredients, for example imidazolinones,sulphonylureas, glyphosates or phosphinothricin (for example the “PAT”gene). The genes which impart the desired properties (“traits”) inquestion may also be present in combinations with one another in thetransgenic plants. Examples of transgenic plants mentioned include theimportant crop plants, such as cereals (wheat, rice, triticale, barley,rye, oats), maize, soybeans, potatoes, sugar beet, sugar cane, tomatoes,peas and other types of vegetable, cotton, tobacco, oilseed rape andalso fruit plants (the fruits being apples, pears, citrus fruits andgrapevines), particular emphasis being given to maize, soybeans, wheat,rice, potatoes, cotton, sugar cane, tobacco and oilseed rape. Properties(“traits”) which are particularly emphasized are the increasedresistance of the plants to insects, arachnids, nematodes and slugs andsnails.

Crop Protection—Types of Treatment

The plants and plant parts are treated with the compounds of the formula(I) or the formula (I′) directly or by action on their surroundings,habitat or storage space using customary treatment methods, for exampleby dipping, spraying, atomizing, irrigating, evaporating, dusting,fogging, broadcasting, foaming, painting, spreading-on, injecting,watering (drenching), drip irrigating and, in the case of propagationmaterial, in particular in the case of seed, additionally by dry seedtreatment, liquid seed treatment, slurry treatment, by incrusting, bycoating with one or more coats, etc. It is furthermore possible to applythe compounds of the formula (I) or the formula (I′) by the ultra-lowvolume method or to inject the application form or the compound of theformula (I) or the formula (I′) itself into the soil.

A preferred direct treatment of the plants is foliar application, i.e.compounds of the formula (I) or the formula (I′) are applied to thefoliage, in which case treatment frequency and the application rateshould be adjusted according to the level of infestation with the pestin question.

In the case of systemically active ingredients, the compounds of theformula (I) or the formula (I′) also gain access to the plants via theroot system. In that case, the plants are treated by the action of thecompounds of the formula (I) or the formula (I′) on the habitat of theplant. This can be accomplished, for example, by drenching, or by mixinginto the soil or the nutrient solution, meaning that the locus of theplant (e.g. soil or hydroponic systems) is impregnated with a liquidform of the compounds of the formula (I) or the formula (I′), or by soilapplication, meaning that the inventive compounds of the formula (I) orthe formula (I′) are introduced in solid form (e.g. in the form ofgranules) into the locus of the plants. In the case of paddy rice crops,this can also be accomplished by metering the compound of the formula(I) or the formula (I′) in a solid application form (for example asgranules) into a flooded paddy field.

Seed Treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvements. However,the treatment of seed entails a series of problems which cannot alwaysbe solved in a satisfactory manner. Thus, it is desirable to developmethods for protecting the seed and the germinating plant which dispensewith, or at least reduce considerably, the additional application ofpesticides during storage, after sowing or after emergence of theplants. It is additionally desirable to optimize the amount of activeingredient used so as to provide optimum protection for the seed and thegerminating plant from attack by animal pests, but without damage to theplant itself by the active ingredient used. In particular, methods forthe treatment of seed should also take account of the intrinsicinsecticidal or nematicidal properties of pest-resistant or -toleranttransgenic plants in order to achieve optimal protection of the seed andalso the germinating plant with a minimum expenditure on pesticides.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants from attack by pests,by treating the seed with one of the compounds of the formula (I) or theformula (I′). The method according to the invention for protecting seedand germinating plants against attack by pests further comprises amethod in which the seed is treated simultaneously in one operation orsequentially with a compound of the formula (I) or the formula (I′) anda mixing component. It further also comprises a method where the seed istreated at different times with a compound of the formula (I) or theformula (I′) and a mixing component.

The invention likewise relates to the use of the compounds of theformula (I) or the formula (I′) for the treatment of seed for protectingthe seed and the resulting plant from animal pests.

The invention further relates to seed which has been treated with aninventive compound of the formula (I) or the formula (I′) for protectionfrom animal pests. The invention also relates to seed which has beentreated simultaneously with a compound of the formula (I) or the formula(I′) and a mixing component. The invention further relates to seed whichhas been treated at different times with a compound of the formula (I)or the formula (I′) and a mixing component. In the case of seed whichhas been treated at different times with a compound of the formula (I)or the formula (I′) and a mixing component, the individual substancesmay be present on the seed in different layers. In this case, the layerscomprising a compound of the formula (I) or the formula (I′) and mixingcomponents may optionally be separated by an intermediate layer. Theinvention also relates to seed in which a compound of the formula (I) orthe formula (I′) and a mixing component have been applied as part of acoating or as a further layer or further layers in addition to acoating.

The invention further relates to seed which, after the treatment with acompound of the formula (I) or the formula (I′), is subjected to afilm-coating process to prevent dust abrasion on the seed.

One of the advantages that occur when one of the compounds of theformula (I) or the formula (I′) acts systemically is that the treatmentof the seed protects not only the seed itself but also the plantsresulting therefrom, after emergence, from animal pests. In this way,the immediate treatment of the crop at the time of sowing or shortlythereafter can be dispensed with.

A further advantage is that the treatment of the seed with a compound ofthe formula (I) or the formula (I′) can enhance germination andemergence of the treated seed.

It is likewise considered to be advantageous that compounds of theformula (I) or the formula (I′) can especially also be used fortransgenic seed.

Compounds of the formula (I) or the formula (I′) can also be used incombination with signalling technology compositions, which results, forexample, in better colonization by symbionts, for example rhizobia,mycorrhizae and/or endophytic bacteria or fungi, and/or in optimizednitrogen fixation.

The compounds of the formula (I) or the formula (I′) are suitable forprotection of seed of any plant variety which is used in agriculture, ingreenhouses, in forests or in horticulture. More particularly, this isthe seed of cereals (for example wheat, barley, rye, millet and oats),maize, cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco,canola, oilseed rape, beets (for example sugar beets and fodder beets),peanuts, vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya beans,cotton, canola, oilseed rape, vegetables and rice.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) or the formula (I′) is also of particularimportance. This involves the seed of plants which generally contain atleast one heterologous gene which controls the expression of apolypeptide having insecticidal and/or nematicidal properties inparticular. The heterologous genes in transgenic seed may originate frommicroorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia,Trichoderma, Clavibacter, Glomus or Gliocladium. The present inventionis particularly suitable for treatment of transgenic seed whichcomprises at least one heterologous gene originating from Bacillus sp.The heterologous gene is more preferably derived from Bacillusthuringiensis.

In the context of the present invention, the compound of the formula (I)or the formula (I′) is applied to the seed. The seed is preferablytreated in a state in which it is sufficiently stable for no damage tooccur in the course of treatment. In general, the seed can be treated atany time between harvest and sowing. It is customary to use seed whichhas been separated from the plant and freed from cobs, shells, stalks,coats, hairs or the flesh of the fruits. For example, it is possible touse seed which has been harvested, cleaned and dried down to a moisturecontent which allows storage. Alternatively, it is also possible to useseed which, after drying, has been treated with, for example, water andthen dried again, for example priming. In the case of rice seed, it isalso possible to use seed which has been soaked, for example in water,until it reaches a certain stage of the rice embryo (“pigeon breaststage”) which results in stimulation of germination and more uniformemergence.

In general, in the treatment of the seed, it has to be ensured that theamount of the compound of the formula (I) and/or the formula (I′) and/orfurther additives applied to the seed is chosen such that thegermination of the seed is not impaired and the plant which arisestherefrom is not damaged. This has to be ensured particularly in thecase of active ingredients which can exhibit phytotoxic effects atcertain application rates.

The compounds of the formula (I) or the formula (I′) are generallyapplied to the seed in a suitable formulation. Suitable formulations andprocesses for seed treatment are known to the person skilled in the art.

The compounds of the formula (I) or the formula (I′) can be converted tothe customary seed-dressing formulations, such as solutions, emulsions,suspensions, powders, foams, slurries or other coating compositions forseed, and also ULV formulations.

These formulations are prepared in a known manner, by mixing thecompounds of the formula (I) or the formula (I′) with customaryadditives, for example customary extenders and solvents or diluents,dyes, wetting agents, dispersants, emulsifiers, antifoams,preservatives, secondary thickeners, adhesives, gibberellins, and alsowater.

Dyes which may be present in the seed-dressing formulations usable inaccordance with the invention are all dyes which are customary for suchpurposes. It is possible to use either pigments, which are sparinglysoluble in water, or dyes, which are soluble in water. Examples includethe dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I.Solvent Red 1.

Useful wetting agents which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofactive agrochemical ingredients. Usable with preference are alkylnaphthalenesulphonates, such as diisopropyl or diisobutylnaphthalenesulphonates.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations usable in accordance with the invention areall nonionic, anionic and cationic dispersants customary for theformulation of active agrochemical ingredients. Nonionic or anionicdispersants or mixtures of nonionic or anionic dispersants can be usedwith preference. Suitable nonionic dispersants especially includeethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristyrylphenol polyglycol ethers, and the phosphated orsulphated derivatives thereof. Suitable anionic dispersants areespecially lignosulphonates, polyacrylic acid salts andarylsulphonate-formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usablein accordance with the invention are all foam-inhibiting substancescustomary for the formulation of active agrochemical ingredients.Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed-dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed-dressing formulationsusable in accordance with the invention are all customary binders usablein seed-dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed-dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz- and Schädlingsbekämpfungsmittel” [Chemistryof Crop Protection Compositions and Pesticides], vol. 2, SpringerVerlag, 1970, p. 401-412).

The seed-dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats, and triticale, and also the seed of maize, rice, oilseedrape, peas, beans, cotton, sunflowers, soya beans and beets, or else awide variety of different vegetable seed. The seed-dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For the treatment of seed with the seed-dressing formulations usable inaccordance with the invention, or the use forms prepared therefrom, allmixing units usable customarily for the seed dressing are useful.Specifically, the procedure in seed dressing is to place the seed into amixer in batchwise or continuous operation, to add the particulardesired amount of seed-dressing formulations, either as such or afterprior dilution with water, and to mix until the formulation isdistributed homogeneously on the seed. If appropriate, this is followedby a drying operation.

The application rate of the seed dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) or the formula (I′) in the formulations and by the seed. Theapplication rates of the compound of the formula (I) or the formula (I′)are generally between 0.001 and 50 g per kilogram of seed, preferablybetween 0.01 and 15 g per kilogram of seed.

Animal Health

In the animal health field, i.e. the field of veterinary medicine, thecompounds of the formula (I) or the formula (I′) are active againstanimal parasites, in particular ectoparasites or endoparasites. The term“endoparasite” includes especially helminths and protozoa, such ascoccidia. Ectoparasites are typically and preferably arthropods,especially insects or acarids.

In the field of veterinary medicine, the compounds of the formula (I) orthe formula (I′) having favourable homeotherm toxicity are suitable forcontrolling parasites which occur in animal breeding and animalhusbandry in livestock, breeding animals, zoo animals, laboratoryanimals, experimental animals and domestic animals. They are activeagainst all or specific stages of development of the parasites.

Agricultural livestock include, for example, mammals, such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deerand especially cattle and pigs; or poultry such as turkeys, ducks, geeseand especially chickens; or fish or crustaceans, for example inaquaculture; or, as the case may be, insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,caged birds, reptiles, amphibians or aquarium fish.

In a particular embodiment, the compounds of the formula (I) or theformula (I′) are administered to mammals.

In another particular embodiment, the compounds of the formula (I) orthe formula (I′) are administered to birds, namely caged birds andparticularly poultry.

Use of the compounds of the formula (I) or the formula (I′) for thecontrol of animal parasites is intended to reduce or prevent illness,cases of deaths and reductions in performance (in the case of meat,milk, wool, hides, eggs, honey and the like), such that more economicaland simpler animal keeping is enabled and better animal well-being isachievable.

In relation to the field of animal health, the term “control” or“controlling” in the present context means that the compounds of theformula (I) or the formula (I′) are effective in reducing the incidenceof the particular parasite in an animal infected with such parasites toan innocuous degree. More specifically, “controlling” in the presentcontext means that the compounds of the formula (I) or the formula (I′)kill the respective parasite, inhibit its growth, or inhibit itsproliferation.

The arthropods include, but are not limited to,

from the order of Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.;

from the order of Mallophagida and the suborders Amblycerina andIschnocerina, for example, Bovicola spp., Damalina spp., Felicola spp.;Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp.,Trinoton spp., Werneckiella spp;

from the order of Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Atylotus spp.,Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culexspp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp.,Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp.,Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Luciliaspp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp.,Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp.,Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanusspp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.;

from the order of Siphonapterida, for example, Ceratophyllus spp.,Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.;

from the order of Heteropterida, for example Cimex spp., Panstrongylusspp., Rhodnius spp., Triatoma spp.; and also nuisance and hygiene pestsfrom the order Blattarida.

In addition, in the case of the arthropods, mention should be made,without limitation, of the following Acari:

from the subclass of Acari (Acarina) and the order of Metastigmata, forexample from the family of Argasidae such as Argas spp., Ornithodorusspp., Otobius spp., from the family of Ixodidae such as Amblyomma spp.,Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp.,Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genusof multi-host ticks); from the order of Mesostigmata such as Dermanyssusspp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp.,Sternostoma spp., Tropilaelaps spp., Varroa spp.; from the order of theActinedida (Prostigmata), for example, Acarapis spp., Cheyletiella spp.,Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp.,Ornithocheyletia spp., Psorergates spp., Trombicula spp.; and from theorder of the Acaridida (Astigmata), for example, Acarus spp.,Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp.,Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp.,Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp.,Tyrophagus spp.

Examples of parasitic protozoa include, but are not limited to:

Mastigophora (Flagellata), such as:

Metamonada: from the order of Diplomonadida, for example Giardia spp.,Spironucleus spp.

Parabasala: from the order of Trichomonadida, for example Histomonasspp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp.,Tritrichomonas spp.

Euglenozoa: from the order of Trypanosomatida, for example Leishmaniaspp., Trypanosoma spp.

Sarcomastigophora (Rhizopoda) such as Entamoebidae, for exampleEntamoeba spp., Centramoebidae, for example Acanthamoeba sp.,Euamoebidae, e.g. Hartmanella sp.

Alveolata such as Apicomplexa (Sporozoa): e.g. Cryptosporidium spp.;from the order of Eimeriida, for example, Besnoitia spp., Cystoisosporaspp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp.,Sarcocystis spp., Toxoplasma spp.; from the order of Adeleida, forexample, Hepatozoon spp., Klossiella spp.; from the order ofHaemosporida, for example, Leucocytozoon spp., Plasmodium spp.; from theorder of Piroplasmida, for example, Babesia spp., Ciliophora spp.,Echinozoon spp., Theileria spp.; from the order of Vesibuliferida, forexample, Balantidium spp., Buxtonella spp.

Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidiumspp., Nosema spp., and also, for example, Myxozoa spp.

The helminths that are pathogenic to humans or animals include, forexample, Acanthocephala, Nematoden, Pentastoma and Platyhelminthes (e.g.Monogenea, cestodes and trematodes).

Illustrative helminths include, but are not limited to,

Monogenea: for example: Dactylogyrus spp., Gyrodactylus spp.,Microbothrium spp., Polystoma spp., Troglecephalus spp.;

Cestodes: from the order of Pseudophyllidea, for example: Bothridiumspp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp.,Ligula spp., Schistocephalus spp., Spirometra spp.

From the order of Cyclophyllida, for example: Andyra spp., Anoplocephalaspp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp.,Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp.,Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp.,Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephalaspp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp.,Thysanosoma spp.

Trematodes: from the class of Digenea, for example: Austrobilharziaspp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchisspp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoeliumspp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp.,Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp.,Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp.,Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeumspp., Leucochloridium spp., Metagonimus spp., Metorchis spp.,Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharziaspp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp.,Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp.,Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

Nematodes: from the order of Trichinellida, for example: Capillariaspp., Trichinella spp., Trichomosoides spp., Trichuris spp.

From the order of Tylenchida, for example: Micronema spp.,Parastrangyloides spp., Strongyloides spp.

From the order of Rhabditida, for example: Aelurostrongylus spp.,Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonemaspp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp.,Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomumspp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp.,Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroidesspp., Globocephalus spp., Graphidium spp., Gyalocephalus spp.,Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagiaspp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirusspp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp.,Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.;Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperiaspp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp.,Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp.,Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylusspp., Syngamus spp., Teladorsagia spp., Trichonema spp.,Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp.,Uncinaria spp.

From the order of Spirurida, for example: Acanthocheilonema spp.,Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculurisspp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp.,Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.;Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp.,Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loaspp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp.,Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp.,Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp.,Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp.,Toxascaris spp., Toxocara spp., Wuchereria spp.

Acanthocephala: from the order of Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order ofMoniliformida, for example: Moniliformis spp.

From the order of Polymorphida, for example: Filicollis spp.; from theorder of Echinorhynchida, for example Acanthocephalus spp.,Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order of Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal husbandry, the compounds of theformula (I) or the formula (I′) are administered by methods generallyknown in the art, such as via the enteral, parenteral, dermal or nasalroute in the form of suitable preparations. Administration may beprophylactic, metaphylactic or therapeutic.

Thus, one embodiment of the present invention refers to the compounds ofthe formula (I) or the formula (I′) for use as a medicament.

A further aspect relates to the compounds of the formula (I) or theformula (I′) for use as an antiendoparasitic agent.

A further specific aspect of the invention relates to the compounds ofthe formula (I) or the formula (I′) for use as an antithelminthic agent,especially for use as a nematicide, platyhelminthicide,acanthocephalizide or pentastomicide.

A further specific aspect relates to the compounds of the formula (I) orthe formula (I′) for use as an antiprotozoic agent.

A further aspect relates to the compounds of the formula (I) or theformula (I′) for use as an antiectoparasitic agent, especially anarthropodicide, very particularly an insecticide or an acaricide.

Further aspects of the invention are veterinary medicine formulationscomprising an effective amount of at least one compound of the formula(I) or the formula (I′) and at least one of the following: apharmaceutically compatible excipient (e.g. solid or liquid diluent), apharmaceutically compatible auxiliary (e.g. surfactants), especially apharmaceutically compatible excipient used conventionally in veterinarymedicine formulations and/or a pharmaceutically compatible auxiliaryconventionally used in veterinary medicine formulations.

A related aspect of the invention is a method for production of aveterinary medicine formulation as described here, which comprises thestep of mixing at least one compound of the formula (I) or the formula(I′) with pharmaceutically compatible excipients and auxiliaries,especially with pharmaceutically compatible excipients usedconventionally in veterinary medicine formulations and/or auxiliariesused conventionally in veterinary medicine formulations.

Another specific aspect of the invention is veterinary medicineformulations selected from the group of ectoparasiticidal andendoparasiticidal formulations, especially selected from the group ofanthelmintic, antiprotozoic and arthropodicidal formulations, veryparticularly selected from the group of nematicidal,platyhelminthicidal, acanthocephalidicidal, pentastomicidal,insecticidal and acaricidal formulations, according to the aboveaspects, and methods for production thereof.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof an effective amount of a compound of the formula (I) or the formula(I′) in an animal, especially a nonhuman animal, having a need therefor.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof a veterinary medicine formulation as defined here in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to the use of the compounds of the formula (I) orthe formula (I′) in the treatment of a parasite infection, especially aninfection caused by a parasite selected from the group of ectoparasitesand endoparasites mentioned here, in an animal, especially a nonhumananimal.

In the present context of animal health or veterinary medicine, the term“treatment” refers to prophylactic, metaphylactic and therapeutictreatment.

In a particular embodiment, in this way, mixtures of at least onecompound of the formula (I) or the formula (I′) with active ingredients,especially with endo- and ectoparasiticides, are provided for the fieldof veterinary medicine.

In the field of animal health, “mixture” means not just that two (ormore) different active ingredients are formulated in a commonformulation and correspondingly employed together, but also relates toproducts comprising formulations separated for each active ingredient.Accordingly, when more than two active ingredients are to be employed,all active ingredients can be formulated in a common formulation or allactive ingredients can be formulated in separate formulations; likewiseconceivable are mixed forms in which some of the active ingredients areformulated together and some of the active ingredients are formulatedseparately. Separate formulations allow the separate or successiveapplication of the active ingredients in question.

The active ingredients specified here by their “common names” are knownand are described, for example, in the “Pesticide Manual” (see above) orcan be searched for on the Internet (e.g.:http://www.alanwood.net/pesticides).

Illustrative active ingredients from the group of the ectoparasiticidesas mixing components, without any intention that this should constitutea restriction, include the insecticides and acaricides listed in detailabove. Further usable active ingredients are listed below in accordancewith the abovementioned classification based on the current IRAC Mode ofAction Classification Scheme: (1) acetylcholinesterase (AChE)inhibitors; (2) GABA-gated chloride channel blockers; (3) sodium channelmodulators; (4) nicotinic acetylcholine receptor (nAChR) competitivemodulators; (5) nicotinic acetylcholine receptor (nAChR) allostericmodulators; (6) glutamate-gated chloride channel (GluCl) allostericmodulators; (7) juvenile hormone mimetics; (8) miscellaneousnon-specific (multi-site) inhibitors; (9) chordotonal organ modulators;(10) mite growth inhibitors; (12) inhibitors of mitochondrial ATPsynthase, such as ATP disruptors; (13) uncouplers of oxidativephosphorylation via disruption of the proton gradient; (14) nicotinicacetylcholine receptor channel blockers; (15) inhibitors of chitinbiosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1;(17) moulting disruptors (especially in Diptera); (18) ecdysone receptoragonists; (19) octopamine receptor agonists; (21) mitochondrial complexI electron transport inhibitors; (25) mitochondrial complex II electrontransport inhibitors; (20) mitochondrial complex III electron transportinhibitors; (22) voltage-dependent sodium channel blockers; (23)inhibitors of acetyl CoA carboxylase; (28) ryanodine receptormodulators;

active ingredients having unknown or non-specific mechanisms of action,e.g. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate,chlordimeform, flubenzimin, dicyclanil, amidoflumet, quinomethionat,triarathene, clothiazoben, tetrasul, potassium oleate, petroleum,metoxadiazone, gossyplur, flutenzine, brompropylate, cryolite;

compounds from other classes, for example butacarb, dimetilan,cloethocarb, phosphocarb, pirimiphos(-ethyl), parathion(-ethyl),methacrifos, isopropyl o-salicylate, trichlorfon, sulprofos, propaphos,sebufos, pyridathion, prothoate, dichlofenthion, demeton-S-methylsulfone, isazofos, cyanofenphos, dialifos, carbophenothion, autathiofos,aromfenvinfos(-methyl), azinphos (-ethyl), chlorpyrifos(-ethyl),fosmethilan, iodofenphos, dioxabenzofos, formothion, fonofos,flupyrazofos, fensulfothion, etrimfos;

organochlorine compounds, for example camphechlor, lindane, heptachlor;or phenylpyrazoles, e.g. acetoprole, pyrafluprole, pyriprole,vaniliprole, sisapronil; or isoxazolines, e.g. sarolaner, afoxolaner,lotilaner, fluralaner;

pyrethroids, e.g. (cis-, trans-)metofluthrin, profluthrin, flufenprox,flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin,RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin,biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin,clocythrin, cyhalothrin (lambda-), chlovaporthrin, or halogenatedhydrocarbon compounds (HCHs),

neonicotinoids, e.g. nithiazine

dicloromezotiaz, triflumezopyrim

macrocyclic lactones, e.g. nemadectin, ivermectin, latidectin,moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate;milbemycin oxime

triprene, epofenonane, diofenolan;

biologicals, hormones or pheromones, for example natural products, e.g.thuringiensin, codlemone or neem components

dinitrophenols, e.g. dinocap, dinobuton, binapacryl;

benzoylureas, e.g. fluazuron, penfluron,

amidine derivatives, e.g. chlormebuform, cymiazole, demiditraz

beehive varroa acaricides, for example organic acids, e.g. formic acid,oxalic acid.

Illustrative active ingredients from the group of the endoparasiticides,as mixing components, include but are not limited to active anthelminticingredients and active antiprotozoic ingredients.

The active anthelmintic ingredients include but are not limited to thefollowing active nematicidal, trematicidal and/or cestocidalingredients:

from the class of the macrocyclic lactones, for example: eprinomectin,abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin,latidectin, milbemectin, ivermectin, emamectin, milbemycin;

from the class of the benzimidazoles and probenzimidazoles, for example:oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole,oxfendazole, netobimin, fenbendazole, febantel, thiabendazole,cyclobendazole, cambendazole, albendazole sulfoxide, albendazole,flubendazole;

from the class of the depsipeptides, preferably cyclic depsipeptides,especially 24-membered cyclic depsipeptides, for example: emodepside,PF1022A;

from the class of the tetrahydropyrimidines, for example: morantel,pyrantel, oxantel;

from the class of the imidazothiazoles, for example: butamisole,levamisole, tetramisole;

from the class of the aminophenylamidines, for example: amidantel,deacylated amidantel (dAMD), tribendimidine;

from the class of the aminoacetonitriles, for example: monepantel;

from the class of the paraherquamides, for example: paraherquamide,derquantel;

from the class of the salicylanilides, for example: tribromsalan,bromoxanide, brotianide, clioxanide, closantel, niclosamide,oxyclozanide, rafoxanide;

from the class of the substituted phenols, for example: nitroxynil,bithionol, disophenol, hexachlorophen, niclofolan, meniclopholan;

from the class of the organophosphates, for example: trichlorfon,naphthalofos, dichlorvos/DDVP, crufomate, coumaphos, haloxon;

from the class of the piperazinones/quinolines, for example:praziquantel, epsiprantel;

from the class of the piperazines, for example: piperazine, hydroxyzine;

from the class of the tetracyclines, for example: tetracycline,chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline;

from various other classes, for example: bunamidine, niridazole,resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquin,mirasan, miracil, lucanthon, hycanthon, hetolin, emetin,diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium,amoscanate, clorsulon.

Active antiprotozoic ingredients include but are not limited to thefollowing active ingredients:

from the class of the triazines, for example: diclazuril, ponazuril,letrazuril, toltrazuril;

from the class of polyether ionophores, for example: monensin,salinomycin, maduramicin, narasin;

from the class of the macrocyclic lactones, for example: milbemycin,erythromycin;

from the class of the quinolones, for example: enrofloxacin,pradofloxacin;

from the class of the quinines, for example: chloroquin;

from the class of the pyrimidines, for example: pyrimethamine;

from the class of the sulphonamides, for example: sulfaquinoxaline,trimethoprim, sulfaclozin;

from the class of the thiamines, for example: amprolium;

from the class of the lincosamides, for example: clindamycin;

from the class of the carbanilides, for example: imidocarb;

from the class of the nitrofurans, for example: nifurtimox;

from the class of the quinazolinone alkaloids, for example:halofuginone;

from various other classes, for example: oxamniquin, paromomycin;

from the class of the vaccines or antigens from microorganisms, forexample: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimerianecatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeriaacervulina, Babesia canis vogeli, Leishmania infantum, Babesia caniscanis, Dictyocaulus viviparus.

All the mixing components mentioned, as the case may be, may also formsalts with suitable bases or acids if they are capable of doing so onthe basis of their functional groups.

Vector Control

The compounds of the formula (I) or the formula (I′) can also be used invector control. In the context of the present invention, a vector is anarthropod, especially an insect or arachnid, capable of transmittingpathogens, for example viruses, worms, single-cell organisms andbacteria, from a reservoir (plant, animal, human, etc.) to a host. Thepathogens can be transmitted into a host either mechanically (forexample trachoma by non-stinging flies) to a host or after injection(for example malaria parasites by mosquitoes).

Examples of vectors and the diseases or pathogens they transmit are:

1) mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of other worms;    -   Aedes: yellow fever, dengue fever, further viral disorders,        filariasis;    -   Simuliidae: transmission of worms, especially Onchocerca        volvulus;    -   Psychodidae: transmission of leishmaniasis

2) Lice: skin infections, epidemic typhus;

3) Fleas: plague, endemic typhus, tapeworms;

4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterialdiseases;

5) Mites: acariosis, epidemic typhus, rickettsialpox, tularaemia, SaintLouis encephalitis, tick-borne encephalitis (TBE), Crimean-Congohaemorrhagic fever, borreliosis;

6) Ticks: borellioses such as Borrelia bungdorferi sensu lato., Borreliaduttoni, tick-borne encephalitis, Q fever (Coxiella burnetii),babesioses (Babesia canis canis), ehrlichiosis.

Examples of vectors in the context of the present invention are insects,for example aphids, flies, leafhoppers or thrips, which can transmitplant viruses to plants. Other vectors capable of transmitting plantviruses are spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, Psychodidae such as Phlebotomus, Lutzomyia,lice, fleas, flies, mites and ticks, which can transmit pathogens toanimals and/or humans.

Vector control is also possible if the compounds of the formula (I) orthe formula (I′) are resistance-breaking.

Compounds of the formula (I) or the formula (I′) are suitable for use inthe prevention of diseases and/or pathogens transmitted by vectors.Thus, a further aspect of the present invention is the use of compoundsof the formula (I) or the formula (I′) for vector control, for examplein agriculture, in horticulture, in forests, in gardens and in leisurefacilities, and also in the protection of materials and stored products.

Protection of Industrial Materials

The compounds of the formula (I) or the formula (I′) are suitable forprotecting industrial materials against attack or destruction byinsects, for example from the orders of Coleoptera, Hymenoptera,Isoptera, Lepidoptera, Psocoptera and Zygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) or the formula(I′) are used together with at least one further insecticide and/or atleast one fungicide.

In a further embodiment, the compounds of the formula (I) or the formula(I′) take the form of a ready-to-use pesticide, meaning that they can beapplied to the material in question without further modifications.Useful further insecticides or fungicides especially include thosementioned above.

It has also been found that, surprisingly, the compounds of the formula(I) or the formula (I′) can be used to protect objects which come intocontact with saltwater or brackish water, especially hulls, screens,nets, buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of the formula (I) or the formula(I′), alone or in combinations with other active ingredients, asantifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) or the formula (I′) are suitable forcontrolling animal pests in the hygiene sector. More particularly, theinvention can be used in the domestic protection sector, in the hygieneprotection sector and in the protection of stored products, particularlyfor control of insects, arachnids, ticks and mites encountered inenclosed spaces, for example dwellings, factory halls, offices, vehiclecabins, animal breeding facilities. For control of animal pests, thecompounds of the formula (I) or the formula (I′) are used alone or incombination with other active ingredients and/or auxiliaries. They arepreferably used in domestic insecticide products. The compounds of theformula (I) or the formula (I′) are effective against sensitive andresistant species, and against all developmental stages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is effected, for example, in aerosols, unpressurized sprayproducts, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or bait stations.

PREPARATION EXAMPLES3-Ethylsulphonyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline(I-1)

800 mg (2.06 mmol) of3-ethylsulphanyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinolinewere dissolved in 200 ml of dichloromethane, 948 mg (20.5 mmol) offormic acid and 2.00 g (20.5 mmol) of hydrogen peroxide were added atroom temperature, and then the mixture was stirred at room temperaturefor 5 h. The mixture was diluted with water, sodium bisulphite solutionwas added, the mixture was stirred for 1 h, and then 10% sodiumhydrogencarbonate solution was added. The organic phase was separatedoff, the aqueous phase was extracted twice with dichloromethane and thecombined organic phases were then freed of the solvent under reducedpressure. The residue was purified by column chromatography purificationby means of preparative HPLC with a water/acetonitrile gradient aseluent.

(log P (neutral): 2.75; MH⁺: 421; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.23(t, 3H), 3.83 (q, 2H), 3.93 (s, 3H), 7.97 (t, 1H), 8.15 (t, 1H), 8.29(d, 1H), 8.33 (s, 1H), 8.51 (d, 1H), 9.32 (s, 1H), 9.34 (s, 1H).

3-Ethylsulphanyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline(I-2)

800 mg (2.20 mmol) of3-chloro-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinolineand 557 mg (6.61 mmol) of sodium ethanethiolate were stirred in DMF atroom temperature under argon for 4 h. Water was added and the mixturewas extracted twice with ethyl acetate. The combined organic phases werewashed with a sodium chloride solution, removed, dried over sodiumsulphate and freed of the solvent under reduced pressure.

(log P (neutral): 3.30; MH⁺: 389; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.27(t, 3H), 3.12 (q, 2H), 4.03 (s, 3H), 7.74-7.84 (m, 2H), 8.08-8.11 (m,2H), 8.32 (s, 1H), 8.58 (s, 1H), 9.29 (s, 1H).

3-Chloro-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline(V-1)

450 mg (2.35 mmol) of N³-methyl-6-(trifluoromethyl)pyridine-3,4-diamine,489 g (2.35 mmol) of 3-chloroquinoline-2-carboxylic acid and 451 mg(2.35 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDCI) were stirred in 6 ml of pyridine at 120° C. for 9h. The reaction mixture was freed of the solvent under reduced pressure,then water was added and the mixture was extracted three times withethyl acetate. The combined organic phases were dried over sodiumsulphate and concentrated again.

The residue was dissolved in 15 ml of toluene, 582 mg (3.06 mmol) ofpara-toluenesulphonic acid were added, and the mixture was stirred at80° C. for 1 h and 120° C. for 3 h. Subsequently, the reaction mixturewas admixed with saturated sodium hydrogencarbonate solution andextracted twice with ethyl acetate. The combined organic phases weredried over sodium sulphate and freed of the solvent under reducedpressure.

(log P (neutral): 2.89; MH⁺: 363; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 4.03(s, 3H), 7.83-7.87 (m, 1H), 7.93-7.97 (m, 1H), 8.15-8.19 (m, 1H), 8.33(s, 1H), 8.95 (s, 1H), 9.31 (s, 1H).

2-Ethylsulphonyl-3-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoxaline(I-3)

160.7 mg (0.41 mmol) of3-ethylsulphanyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoxalinewere dissolved in 10 ml of dichloromethane, 195.1 mg (0.82 mmol) ofmeta-chloroperbenzoic acid were added at 0° C., and the mixture wasstirred at 0° C. for 5 min and at room temperature for 2 h. The mixturewas admixed with sodium bisulphite solution, stirred for 1 h, dilutedwith 20 ml of water and adjusted to pH 9-10 with 45% sodium hydroxidesolution. Then the mixture was extracted three times withdichloromethane and then the combined organic phases were freed of thesolvent under reduced pressure.

(log P (neutral): 2.45; MH⁺: 422; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.28(t, 3H), 3.82 (q, 2H), 4.00 (s, 3H), 8.22-8.26 (m, 2H), 8.33 (s, 1H),8.38-8.40 (m, 1H), 8.45-8.47 (m, 1H), 9.32 (s, 1H).

2-Ethylsulphanyl-3-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoxaline(I-4)

280 mg (0.66 mmol) of2-chloro-3-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoxalineand 111.4 mg (1.32 mmol) of sodium ethanethiolate were stirred in 8 mlof DMF at room temperature under argon for 30 min. Water was added andthe mixture was extracted twice with ethyl acetate. The combined organicphases were washed with a sodium chloride solution, removed, dried oversodium sulphate and freed of the solvent under reduced pressure. Theresidue was purified by column chromatography purification with acyclohexane/ethyl acetate gradient as eluent.

(log P (neutral): 4.10; MH⁺: 390; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.37(t, 3H), 3.31 (q, 2H), 4.18 (s, 3H), 7.85 (t, 1H), 7.96 (t, 1H), 8.08(d, 1H), 8.16 (d, 1H), 8.37 (s, 1H), 9.33 (s, 1H).

2-Chloro-3-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoxaline(V-2)

385 mg (2.01 mmol) of N³-methyl-6-(trifluoromethyl)pyridine-3,4-diamine,504 mg (2.41 mmol) of 3-chloroquinoxaline-2-carboxylic acid and 386 mg(2.01 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDCI) were stirred in 10 ml of pyridine at roomtemperature for 18 h. The reaction mixture was freed of the solventunder reduced pressure, then water was added and the mixture wasextracted three times with ethyl acetate. The combined organic phaseswere dried over sodium sulphate and concentrated again.

The residue was dissolved in 5 ml of toluene, 181.3 mg (0.95 mmol) ofpara-toluenesulphonic acid were added, and the mixture was stirred at120° C. for 2 h. Subsequently, the reaction mixture was admixed withsaturated sodium hydrogencarbonate solution and extracted twice withethyl acetate. The combined organic phases were dried over sodiumsulphate and freed of the solvent under reduced pressure.

(log P (neutral): 2.84; MH⁺: 364; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 4.12(s, 3H), 8.03-8.13 (m, 2H), 8.22-8.31 (m, 2H), 8.37 (s, 1H), 9.33 (s,1H).

6-(3-Ethylsulphonyl-2-quinolyl)-2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazole

13 mg (0.03 mmol) of6-(3-ethylsulphonyl-2-quinolyl)-2,2-difluoro-5H-[1,3]dioxolo[4,5-f]benzimidazole,4.9 mg (0.03 mmol) of methyl iodide and 8.6 mg (0.06 mmol) of potassiumcarbonate were dissolved in 3 ml of acetone and stirred under reflux for3 h. The reaction mixture was filtered off, the mother liquor was freedof the solvent, the residue was taken up in dichloromethane, washed withwater, dried over sodium sulphate and then the solvent was distilled offunder reduced pressure.

(log P (neutral): 3.39; MH⁺: 432; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.23(t, 3H), 3.76 (s, 3H), 3.90 (q, 2H), 7.80 (s, 1H), 7.91 (s, 1H), 7.93(t, 1H), 8.12 (t, 1H), 8.25 (d, 1H), 8.47 (d, 1H), 9.28 (s, 1H).

6-(3-Ethylsulphonyl-2-quinolyl)-2,2-difluoro-5H-[1,3]dioxolo[4,5-f]benzimidazole

26 mg (0.06 mmol) of6-(3-ethylsulphanyl-2-quinolyl)-2,2-difluoro-5H-[1,3]dioxolo[4,5-f]benzimidazolewere dissolved in 3 ml of dichlormethane, 9.2 mg (0.20 mmol) of formicacid and 45.4 mg (0.46 mmol) of 35% hydrogen peroxide were added at roomtemperature, and then the mixture was stirred at room temperature for 4h. Subsequently, 3 further equivalents of formic acid and 7 equivalentsof 35% hydrogen peroxide were added and the mixture was stirred at roomtemperature for a further 2 h. The reaction mixture was diluted withwater and admixed with sodium bisulphite solution, stirred for 30 min,and then admixed with saturated sodium hydrogencarbonate solution. Theorganic phase was separated off, the aqueous phase was extracted twicewith dichloromethane, and the combined organic phases were then freed ofthe solvent under reduced pressure. The residue was purified by columnchromatography purification with a cyclohexane/ethyl acetate gradient(70:30 to 30:70) as eluent.

(log P (neutral): 3.37; MH⁺: 418; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.30(t, 3H), 4.31 (q, 2H), 7.63 (br. s, 1H), 7.80 (br. s, 1H), 7.89 (t, 1H),8.10 (t, 1H), 8.24 (d, 1H), 8.43 (d, 1H), 9.27 (s, 1H), 13.54 (s, 1H).

6-(3-Ethylsulphanyl-2-quinolyl)-2,2-difluoro-5H-[1,3]dioxolo[4,5-f]benzimidazole

590 mg (2.97 mmol) of 2,2-difluoro-1,3-benzodioxole-5,6-diamine, 926.7mg (3.57 mmol) of 3-ethylsulphanylquinoline-2-carboxylic acid, 576.9 mg(2.97 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDCI) and 4.4 mg of molecular sieve (4 A) were stirred in30 ml of pyridine under argon at 120° C. for 8 h. The reaction mixturewas freed of solvent under reduced pressure, and the residue was takenup in ethyl acetate and washed with water. The aqueous phase wasextracted twice with ethyl acetate, the organic phases were combined anddried over sodium sulphate, and then the solvent was distilled off underreduced pressure. The residue was stirred at reflux in 30 ml ofphosphoryl chloride for 4 h and then the solvent was removed again underreduced pressure. The residue was taken up in dichloromethane, washedwith water and dried over sodium sulphate, and then the solvent wasdistilled off under reduced pressure. The residue was purified by columnchromatography purification with a cyclohexane/ethyl acetate gradient(70:30 to 0:100) as eluent.

(log P (neutral): 4.26; MH⁺: 386; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.39(t, 3H), 3.14 (q, 2H), 7.56 (br. s, 1H), 7.66 (t, 1H), 7.76 (t, 1H),7.84 (br. s, 1H), 8.02 (d, 1H), 8.07 (d, 1H), 8.37 (s, 1H), 13.31 (s,1H).

2-(3-Ethylsulphonyl-2-quinolyl)-5-(trifluoromethylsulphonyl)-1,3-benzoxazole

103 mg (0.06 mmol) of2-(3-ethylsulphonyl-2-quinolyl)-5-(trifluoromethylsulphanyl)-1,3-benzoxazolewere dissolved in 12 ml of dichlormethane, 182 mg (3.93 mmol) of formicacid and 1.81 g (18.59 mmol) of 35% hydrogen peroxide were added at roomtemperature, and then the mixture was stirred at 40° C. for 72 h. Thereaction mixture was diluted with water and admixed with sodiumbisulphite solution, stirred for 30 min, and then admixed with saturatedsodium hydrogencarbonate solution. The organic phase was separated off,the aqueous phase was extracted twice with dichloromethane and thecombined organic phases were then freed of the solvent under reducedpressure. The residue was purified by column chromatography with adichloromethane/ethyl acetate gradient (0:100 to 40:60) as eluent.

(log P (neutral): 3.62; MH⁺: 471; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.33(t, 3H), 4.00 (q, 2H), 8.00 (t, 1H), 8.18 (t, 1H), 8.32-8.37 (m, 2H),8.45 (d, 1H), 8.51 (d, 1H), 8.87 (s, 1H), 9.40 (s, 1H).

2-(3-Ethylsulphonyl-2-quinolyl)-5-(trifluoromethylsulphinyl)-1,3-benzoxazole

The same method as described for the synthesis of2-(3-ethylsulphonyl-2-quinolyl)-5-(trifluoromethylsulphonyl)-1,3-benzoxazolewas also used to obtain the corresponding trifluoromethylsulphoxidederivative2-(3-ethylsulphonyl-2-quinolyl)-5-(trifluoromethylsulphinyl)-1,3-benzoxazole.

(log P (neutral): 3.05; MH⁺: 455; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.32(t, 3H), 3.99 (q, 2H), 7.99 (t, 1H), 8.11-8.18 (m, 2H), 8.32-8.34 (m,2H), 8.50 (d, 1H), 8.55 (s, 1H), 9.38 (s, 1H).

2-(3-Ethylsulphonyl-2-quinolyl)-5-(trifluoromethylsulphanyl)-1,3-benzoxazole

244 mg (0.57 mmol) of2-(3-ethylsulphanyl-2-quinolyl)-5-(trifluoromethylsulphanyl)-1,3-benzoxazolewere dissolved in 16 ml of dichloromethane, 157.5 mg (3.42 mmol) offormic acid and 554.0 mg (5.7 mmol) of 35% hydrogen peroxide were addedat room temperature, and then the mixture was stirred at roomtemperature for 6 h. The reaction mixture was diluted with water andadmixed with sodium bisulphite solution, stirred for 30 min, and thenadmixed with saturated sodium hydrogencarbonate solution. The organicphase was separated off, the aqueous phase was extracted twice withdichloromethane and the combined organic phases were then freed of thesolvent under reduced pressure. The residue was purified by columnchromatography purification with a cyclohexane/ethyl acetate gradient(70:30 to 0:100) as eluent.

(log P (neutral): 4.17; MH⁺: 439; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.32(t, 3H), 3.98 (q, 2H), 7.93-8.00 (m, 2H), 8.13-8.18 (m, 2H), 8.31 (d,1H), 8.40 (s, 1H), 8.50 (d, 1H), 9.37 (s, 1H).

2-(3-Ethylsulphanyl-2-quinolyl)-5-(trifluoromethylsulphanyl)-1,3-benzoxazole

446 mg (2.02 mmol) of 2-amino-4-(trifluoromethylsulphanyl)phenol, 708.8mg (2.43 mmol) of 3-ethylsulphanylquinoline-2-carboxylic acid and 465.9mg (2.97 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDCI) were stirred in 20 ml of pyridine under argon at80° C. for 4 h. The reaction mixture was freed of the solvent underreduced pressure and the residue was purified by column chromatographypurification with cyclohexane/ethyl acetate as eluent.

540 mg (1.17 mmol) of the 3-ethylsulphanyl-N-[2-hydroxy-5-(trifluoromethylsulphanyl)phenyl]quinoline-2-carboxamideintermediate prepared in this way were stirred in 30 ml oftetrahydrofuran in the presence of 409 mg (1.68 mmol) ofdi-2-methoxyethyl azodicarboxylate (DMEAD) and 434 mg oftriphenylphospine at room temperature for 1 h and at 50° C. for 1 h.Subsequently, the reaction mixture was freed of the solvent underreduced pressure and the residue was purified by column chromatographypurification with a cyclohexane/ethyl acetate gradient (80:20 to 40:60)as eluent.

(log P (neutral): 5.43; MH⁺: 407; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.38(t, 3H), 3.21 (q, 2H), 7.73-7.82 (m, 2H), 7.90 (d, 1H), 8.07-8.15 (m,3H), 8.41 (s, 1H), 8.54 (s, 1H).

3-Ethylsulphonyl-2-[1-methyl-5-(trifluoromethylsulphonyl)benzimidazol-2-yl]quinoline

71 mg (0.15 mmol) of3-ethylsulphonyl-2-[1-methyl-5-(trifluoromethylsulphinyl)benzimidazol-2-yl]quinolinewere dissolved in 6 ml of acetonitrile, 10.0 mg (0.02 mmol) of sodiumtungstate(VI) dihydrate and 738.0 mg (7.58 mmol) of 35% hydrogenperoxide were added at room temperature, and then the mixture wasstirred at reflux for 24 h. The reaction mixture was diluted with waterand admixed with sodium bisulphite solution, stirred for 30 min, andthen admixed with saturated sodium hydrogencarbonate solution. Theorganic phase was separated off, the aqueous phase was extracted twicewith dichloromethane and the combined organic phases were then freed ofthe solvent under reduced pressure. The residue was purified by columnchromatography purification with a dichloromethane/ethyl acetategradient (70:30 to 0:100) as eluent.

(log P (neutral): 3.42; MH⁺: 484; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.24(t, 3H), 3.87 (q, 2H), 3.89 (s, 3H), 7.97 (t, 1H), 8.10-8.28 (m, 4H),8.50 (d, 1H), 8.56 (s, 1H), 9.34 (s, 1H).

3-Ethylsulphonyl-2-[1-methyl-5-(trifluoromethylsulphinyl)benzimidazol-2-yl]quinoline

262 mg (0.62 mmol) of3-ethylsulphanyl-2-[1-methyl-5-(trifluoromethylsulphanyl)benzimidazol-2-yl]quinolinewere dissolved in 6 ml of dichloromethane, 143.7 mg (3.12 mmol) offormic acid and 424.9 mg (4.37 mmol) of 35% hydrogen peroxide were addedat room temperature, and then the mixture was stirred at roomtemperature for 4 h. The reaction mixture was diluted with water andadmixed with sodium bisulphite solution, stirred for 30 min, and thenadmixed with saturated sodium hydrogencarbonate solution. The organicphase was separated off, the aqueous phase was extracted twice withdichloromethane and the combined organic phases were then freed of thesolvent under reduced pressure. The residue was purified by columnchromatography purification with a cyclohexane/ethyl acetate gradient(80:20 to 0:100) as eluent.

(log P (neutral): 2.79; MH⁺: 468; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.24(t, 3H), 3.85 (s, 1H), 3.90 (q, 2H), 7.91-7.97 (m, 2H), 8.10-8.15 (m,2H), 8.26 (d, 1H), 8.34 (s, 1H), 8.50 (d, 1H), 9.32 (s, 1H).

3-Ethylsulphonyl-2-[1-methyl-5-(trifluoromethylsulphanyl)benzimidazol-2-yl]quinoline

The same method as described for the synthesis of3-ethylsulphonyl-2-[1-methyl-5-(trifluoromethylsulphinyl)benzimidazol-2-yl]quinolinewas also used to obtain the corresponding trifluoromethylsulphidederivative3-ethylsulphonyl-2-[1-methyl-5-(trifluoromethylsulphanyl)benzimidazol-2-yl]quinoline.

(log P (neutral): 3.96; MH⁺: 452; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.23(t, 3H), 3.80 (s, 1H), 3.90 (q, 2H), 7.71 (d, 1H), 7.90-7.97 (m, 2H),8.11-8.15 (m, 2H), 8.26 (d, 1H), 8.49 (d, 1H), 9.31 (s, 1H).

3-Ethylsulphanyl-2-[1-methyl-5-(trifluoromethylsulphanyl)benzimidazol-2-yl]quinoline

806 mg (3.37 mmol) ofN1-methyl-4-(trifluoromethylsulphanyl)phenylene-1,2-diamine, 966.5 mg(4.04 mmol) of 3-ethylsulphanylquinoline-2-carboxylic acid, 673.0 mg(3.37 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDCI) and 4 mg of molecular sieve (4 A) were stirred in30 ml of pyridine under argon at 120° C. for 8 h. The reaction mixturewas freed of solvent under reduced pressure, and the residue was takenup in ethyl acetate and washed once with water. The aqueous phase wasextracted twice with ethyl acetate, the combined organic phases weredried over sodium sulphate and the solvent was then distilled off underreduced pressure. The residue was purified by column chromatographypurification with a water/acetonitrile gradient plus 0.1 ml/l formicacid as eluent.

(log P (neutral): 4.63; MH⁺: 420; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.27(t, 3H), 3.11 (q, 2H), 3.91 (s, 1H), 7.69-7.80 (m, 4H), 7.89 (d, 1H),8.07 (d, 1H), 8.16 (s, 1H), 8.53 (s, 1H).

2-(3-Ethylsulphonyl-2-quinolyl)-6-methyloxazolo[5,4-b]pyridine

86 mg (0.21 mmol) of2-(3-ethylsulphanyl-2-quinolyl)-6-methyloxazolo[5,4-b]pyridine weredissolved in 6 ml of dichlormethane, 49.6 mg (1.07 mmol) of formic acidand 188.4 mg (1.93 mmol) of 35% hydrogen peroxide were added at roomtemperature, and then the mixture was stirred at room temperature for 7h. The reaction mixture was diluted with water and admixed with sodiumbisulphite solution, stirred for 30 min, and then admixed with saturatedsodium hydrogencarbonate solution. The organic phase was separated off,the aqueous phase was extracted twice with dichloromethane and thecombined organic phases were then freed of the solvent under reducedpressure. The residue was purified by column chromatography purificationwith a cyclohexane/ethyl acetate gradient (80:20 to 0:100) as eluent.

(log P (neutral): 3.27; MH⁺: 408; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.32(t, 3H), 3.93 (q, 2H), 8.00 (t, 1H), 8.18 (t, 1H), 8.35 (d, 1H), 8.51(d, 1H), 9.03 (s, 1H), 9.04 (s, 1H), 9.40 (s, 1H).

2-(3-Ethylsulphinyl-2-quinolyl)-6-methyloxazolo[5,4-b]pyridine

The same method as described for the synthesis of2-(3-ethylsulphonyl-2-quinolyl)-6-methyloxazolo[5,4-b]pyridine was alsoused to obtain the corresponding sulphoxide derivative2-(3-ethylsulphinyl-2-quinolyl)-6-methyloxazolo[5,4-b]pyridine.

(log P (neutral): 2.98; MH⁺: 492; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.25(t, 3H), 2.93-3.02 (m, 1H), 3.47-3.56 (m, 1H), 7.90 (t, 1H), 8.05 (t,1H), 8.37-8.41 (m, 2H), 8.99 (s, 1H), 9.03 (s, 1H), 9.10 (s, 1H).

2-(3-Ethylsulphanyl-2-quinolyl)-6-methyloxazolo[5,4-b]pyridine

172 mg (0.36 mmol) ofN-(2-chloro-5-methyl-3-pyridyl)-3-ethylsulphanylquinoline-2-carboxamidewere dissolved in 6 ml of dimethylformamide, 38.9 mg (0.36 mmol) ofsodium carbonate were added and the mixture was stirred at 145° C. for 4h. The mixture was added to ice-water and extracted twice with ethylacetate, the combined organic phases were washed with water and driedover sodium sulphate, and the solvent was distilled off under reducedpressure. The residue was purified by column chromatography purificationwith a cyclohexane/ethyl acetate gradient as eluent.

(log P (neutral): 4.36; MH⁺: 376; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.38(t, 3H), 3.22 (q, 2H), 7.75-7.85 (m, 2H), 8.09 (d, 1H), 8.17 (d, 1H),8.55 (s, 1H), 8.97 (s, 1H), 9.01 (s, 1H).

N-(2-Chloro-5-methyl-3-pyridyl)-3-ethylsulphanylquinoline-2-carboxamide(IV-1)

240 mg (1.19 mmol) of 2-chloro-5-(trifluoromethyl)pyridin-3-amine and357 mg (1.31 mmol) of 3-ethylsulphanylquinoline-2-carboxylic acid weredissolved together with 0.39 ml (4.78 mmol) of pyridine in 20 ml ofdioxane, 367 mg (2.39 mmol) of phosphoryl chloride were added, and themixture was stirred at reflux for 90 min. The mixture was concentrated,the residue was taken up in ethyl acetate and washed with water, and theaqueous phase was extracted twice with ethyl acetate. The combinedorganic phases were dried over sodium sulphate and the solvent wasdistilled off under reduced pressure. The residue was purified by columnchromatography purification with a cyclohexane/ethyl acetate gradient(80:20 to 40:60) as eluent.

(log P (neutral): 5.71; MH⁺: 412; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.37(t, 3H), 3.12 (q, 2H), 7.74-7.84 (m, 2H), 8.07-8.14 (m, 2H), 8.49 (s,1H), 8.70 (s, 1H), 9.02 (s, 1H), 11.12 (s, 1H).

3-(Ethylsulphonyl)-2-[7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-2-yl]quinoline

3-(Ethylsulphanyl)-2-[7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-2-yl]quinoline(24 mg, 0.06 mmol) was dissolved in 2 ml of dichloromethane. Hydrogenperoxide (35% aqueous solution, 43 mg, 0.44 mmol) and formic acid (15mg, 0.32 mmol) were added and the reaction mixture was stirred for 12 h.While cooling with ice, 1 ml of 40% sodium bisulphite solution was addeddropwise and the mixture was stirred for 1 h. The phases were separated,and the organic phase was washed with sodium hydrogencarbonate solution,dried over sodium sulphate and concentrated on a rotary evaporator. Theresidue was purified by chromatography (eluent: cyclohexane, ethylacetate).

log P (neutral): 2.63; MH⁺: 407; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 9.70(s, 1H), 9.23 (s, 1H), 8.74 (s, 1H), 8.41-8.39 (m, 2H), 8-21-8.19 (m,1H), 8.08-8.04 (m, 1H), 7.87-7.83 (m, 1H), 4.17-4.12 (m, 2H), 1.30-1.27(m, 3H).

3-(Ethylsulphanyl)-2-[7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-2-yl]quinoline

2-Bromo-1-[3-(ethylsulphanyl)quinolin-2-yl]ethanone (453 mg, 0.92 mmol)and 6-(trifluoromethyl)pyrimidin-4-amine (150 mg, 0.92 mmol) weredissolved in 5 ml of tert-butanol, and sodium hydrogencarbonate (386 mg,4.59 mmol) was added. The reaction mixture was stirred at 80° C. for 5h. After the solvent had been removed on a rotary evaporator, theresidue was purified by chromatography.

log P (neutral): 3.24; MH⁺: 375; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 9.68(s, 1H), 8.80 (s, 1H), 8.37 (s, 2H), 8.02-7.99 (m, 2H), 7.75-7.70 (m,1H), 7.66-7.62 (m, 1H), 3.16-3.10 (m, 2H), 1.34-1.30 (m, 3H).

2-Bromo-1-[3-(ethylsulphanyl)quinolin-2-yl]ethanone

Pyridine hydrobromide perbromide (PyBr₃, 100 mg, 0.43 mmol) wasdissolved in 4 ml of glacial acetic acid. HBr (32% in glacial aceticacid, 0.15 ml) was added and the mixture was stirred at room temperaturefor 30 min. Then 1-[3-(ethylsulphanyl)quinolin-2-yl]ethanone (100 mg,0.43 mmol) dissolved in 1 ml of glacial acetic acid was added dropwise.The reaction mixture was stirred at room temperature for 12 h and thenconcentrated. The residue was taken up with ethyl acetate and washedwith saturated sodium hydrogencarbonate solution and saturated sodiumchloride solution. After the organic phase had been dried over sodiumsulphate, the solvent was removed on a rotary evaporator. The residuewas converted in the subsequent reaction without further purification.

log P (acidic): 3.95; MH⁺: 312

1-[3-(Ethylsulphanyl)quinolin-2-yl]ethanone

Under an argon atmosphere,3-(ethylsulphanyl)-N-methoxy-N-methylquinoline-2-carboxamide (2.8 g, 8.1mmol) was dissolved in 155 ml of dry THF and cooled to 0° C.Methylmagnesium bromide (3M in diethyl ether, 8.1 ml, 24.3 mmol) wasslowly added dropwise, then the mixture was stirred for 2 h at 0° C. Inorder to end the reaction, 5 ml of ammonium chloride solution were addedgradually while cooling. The organic phase was separated off and washedwith saturated sodium chloride solution. The solvent was removed on arotary evaporator and the crude product was used in the subsequentreaction without further purification.

log P (neutral): 3.31; MH⁺: 232; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 8.38(s, 1H), 8.08-8.00 (m, 2H), 7.79-7.70 (m, 2H), 3.10-3.04 (m, 2H), 2.75(s, 3H), 1.35-1.31 (m, 3H).

3-(Ethylsulphanyl)-N-methoxy-N-methylquinoline-2-carboxamide

3-(Ethylsulphanyl)quinoline-2-carboxylic acid (240 mg, 1.02 mmol) andN,O-dimethylhydroxylamine hydrochloride (100 mg, 1.02 mmol) weredissolved in 3 ml of dichloromethane and cooled to 0° C.4-Dimethylaminopyridine (DMAP, 150 mg, 1.23 mmol) andN-(dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI, 217mg, 1.13 mmol) were added and the reaction mixture was stirred for 2 hat 0° C., then for 12 h at room temperature. The solution was washedonce with saturated sodium hydrogencarbonate solution and once withsodium chloride solution, dried over sodium sulphate and concentrated.The crude product was used in the subsequent reaction without furtherpurification.

log P (neutral): 2.17; MH⁺: 277; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 8.46(s, 1H), 8.02-7.98 (m, 2H), 7.78-7.75 (m, 1H), 7.70-7.64 (m, 1H), 3.51(s, 3H), 3.32 (s, 3H), 3.12-3.05 (m, 2H), 1.28-1.24 (m, 3H).

3-(Ethylsulphanyl)quinoline-2-carboxylic acid

Under an argon atmosphere, 2,2,6,6-tetramethylpiperidine (5.34 g, 38mmol) was dissolved in 50 ml of dry THF and cooled to −25° C.n-Butyllithium (2.5 M in hexane, 2.44 g, 38.1 mmol, 15.2 ml) was addeddropwise and the mixture was stirred at −25° C. for 20 min. Thenquinoline-2-carboxylic acid (3.00 g, 17.3 mmol) dissolved in 20 ml ofTHF was added dropwise and the mixture was stirred at −25° C. for afurther 30 min. Diethyl disulphide (5.29 g, 43.3 mmol) was addeddropwise and, after stirring at −25° C. for 30 min, the mixture waswarmed gradually to room temperature. The reaction mixture wasconcentrated on a rotary evaporator and the residue was taken up in 100ml of cyclohexane/diethyl ether (3:7). The remaining solids wereisolated by filtration. Water was added, and 2.5 M HCl solution wasadded until a pH of 4 was obtained. The aqueous solution was extractedthree times with dichloromethane. The combined organic extracts weredried over sodium sulphate and the solvent was removed on a rotaryevaporator. The crude product was used in the subsequent reactionwithout further purification.

log P (neutral): 0.48; MH⁺: 234; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 8.43(s, 1H), 8.03-8.00 (m, 2H), 7.78-7.74 (m, 1H), 7.70-7.67 (m, 1H),3.13-3.07 (m, 2H), 1.32-1.28 (m, 3H).

3,6-Bis(ethylsulphonyl)-2-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]-1,8-naphthyridine

35 mg (0.078 mmol) of3,6-bis(ethylsulphanyl)-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-1,8-naphthyridinewere dissolved in 3.5 ml of dichloromethane, 18 mg (0.39 mmol) of formicacid and 53 mg (0.545 mmol) of hydrogen peroxide were added at roomtemperature, and then the mixture was stirred at room temperature for 18h. The mixture was freed of the solvent under reduced pressure. Theresidue was purified by column chromatography purification with acyclohexane/ethyl acetate gradient as eluent.

log P (neutral): 2.21; MH⁺: 514; ¹H-NMR (400 MHz, CD₃CN) δ ppm: 1.29 (t,3H), 1.33 (t, 3H), 3.41 (q, 2H), 3.92 (q, 2H), 4.00 (s, 3H), 8.22 (s,1H), 9.155 (s, 1H), 9.26 (d, 1H), 9.43 (s, 1H), 9.65 (d, 1H).

3,6-Bis(ethylsulphanyl)-2-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]-1,8-naphthyridine

255 mg (0.493 mmol) of3,6-dichloro-2-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]-1,8-naphthyridineand 156 mg (1.48 mmol) of sodium ethanethiolate were stirred in 14.2 mlof DMF at room temperature under argon for 2 h. Water was added and themixture was extracted twice with ethyl acetate. The combined organicphases were dried over sodium sulphate and freed of the solvent underreduced pressure. The residue was purified by column chromatographypurification with a cyclohexane/ethyl acetate gradient as eluent.

log P (neutral): 3.23; MH⁺: 450; ¹H-NMR (400 MHz, CD₃CN) δ ppm: 1.34 (t,3H), 1.42 (t, 3H), 3.10 (q, 2H), 3.19 (q, 2H), 4.06 (s, 3H), 8.15 (d,1H), 8.18 (s, 1H), 8.29 (s, 1H), 8.92 (d, 1H), 9.10 (s, 1H).

3,6-Dichloro-2-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]-1,8-naphthyridine(V-3)

310 mg (1.62 mmol) of N³-methyl-6-(trifluoromethyl)pyridine-3,4-diamine,512 mg (2.11 mmol) of 3,6-dichloro-1,8-naphthyridine-2-carboxylic acidand 622 mg (3.24 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDCI) were stirred in 18 ml of pyridine at 120° C. for 18h. 140 mg (0.811 mmol) of para-toluenesulphonic acid were added and thereaction mixture was stirred at 120° C. for 18 h. The mixture wasdiluted with acetonitrile, filtered and freed of the solvent underreduced pressure. The residue was purified by column chromatographypurification with a dichloromethane/methanol gradient as eluent.

log P (neutral): 2.44; MH⁺: 398; ¹H-NMR (400 MHz, CD₃CN) δ ppm: 4.03 (s,3H), 8.22 (s, 1H), 8.48 (d, 1H), 8.65 (s, 1H), 9.13 (s, 2H).

3,6-Dichloro-1,8-naphthyridine-2-carboxylic acid (III-1)

990 mg (3.85 mmol) of methyl3,6-dichloro-1,8-naphthyridine-2-carboxylate and 184 mg (7.70 mmol) oflithium hydroxide were stirred in 6.9 ml of tetrahydrofuran and 2.3 mlof water at room temperature for 18 h. An aqueous 1 N chloric acidsolution was added, and the mixture was freed of the solvent underreduced pressure. Toluene was twice added to the residue and the mixturewas freed of the solvent under reduced pressure.

log P (acidic): 0.70; MH⁺: 243; ¹H-NMR (400 MHz, CD₃CN) δ ppm: 8.39 (m,1H), 8.49 (s, 1H), 9.07 (m, 1H).

Methyl 3,6-dichloro-1,8-naphthyridine-2-carboxylate (XXXI-1)

2.37 g (12.6 mmol) of methyl 1,8-naphthyridine-2-carboxylate and 1.93 g(14.5 mmol) of N-chlorosuccinimide were stirred in 118 ml ofacetonitrile at 60° C. for 18 h. The mixture was freed of the solventunder reduced pressure. The residue was purified by columnchromatography purification with an ethyl acetate/methanol gradient aseluent.

log P (neutral): 1.93; MH⁺: 257; ¹H-NMR (400 MHz, CD₃CN) δ ppm: 4.01 (s,3H), 8.71 (d, 1H), 8.845 (s, 1H), 9.20 (d, 1H).

Methyl 1,8-naphthyridine-2-carboxylate (XXII-1)

600 mg (3.44 mmol) of 1,8-naphthyridine-2-carboxylic acid and 0.754 ml(10.3 mmol) of thionyl chloride were stirred in 15 ml of methanol at 60°C. for 6 h. The mixture was freed of the solvent under reduced pressure.Methyl tert-butyl ether was added to the residue and the mixture wasfreed of the solvent under reduced pressure.

log P (neutral): 0.77; MH⁺: 189; ¹H-NMR (400 MHz, CD₃CN) δ ppm: 4.00 (s,3H), 7.84 (dd, 1H), 8.27 (d, 1H), 8.70 (dd, 1H), 8.76 (d, 1H), 9.28 (m,1H).

1,8-Naphthyridine-2-carboxylic acid (XXX-1)

3.00 g (24.6 mmol) of 2-aminonicotinaldehyde and 4.44 ml (49.1 mmol) ofmethyl pyruvate were stirred in 30 ml of ethanol and 5.0 ml of water at0° C. 30 ml (90.0 mmol) of an aqueous 3 N sodium hydroxide solution wereadded and the reaction mixture was stirred at RT for 18 h. The mixturewas adjusted to pH=1 at 0° C. with about 50 ml of an aqueous 1 N chloricacid solution, freed of ethanol under reduced pressure and filtered.

log P (acidic): −0.12; MH⁺: 175; ¹H-NMR (400 MHz, CD₃CN) δ ppm: 7.72(dd, 1H), 8.30 (d, 1H), 8.495 (dd, 1H), 8.62 (d, 1H), 9.22 (m, 1H).

Methyl 3,6-dichloro-1,5-naphthyridine-2-carboxylate (XXXI-2)

1.07 g (5.69 mmol) of methyl 1,5-naphthyridine-2-carboxylate and 873 mg(6.54 mmol) of N-chlorosuccinimide were stirred in 100 ml ofacetonitrile at 60° C. for 18 h. The mixture was freed of the solventunder reduced pressure. The residue was purified by columnchromatography purification with an ethyl acetate/methanol gradient aseluent.

log P (neutral): 2.46; MH⁺: 257; ¹H-NMR (400 MHz, CD₃CN) δ ppm: 4.02 (s,3H), 8.49 (m, 1H), 8.61 (s, 1H), 9.01 (d, 1H).

Methyl 1,5-naphthyridine-2-carboxylate (XXII-2)

1.00 g (5.74 mmol) of 1,5-naphthyridine-2-carboxylic acid and 1.26 ml(17.2 mmol) of thionyl chloride were stirred in 15 ml of methanol at 60°C. for 6 h. The mixture was freed of the solvent under reduced pressure.Methyl tert-butyl ether was added to the residue and the mixture wasfreed of the solvent under reduced pressure.

log P (neutral): 0.92; MH⁺: 189; ¹H-NMR (400 MHz, CD₃CN) δ ppm: 4.04 (s,3H), 8.19 (dd, 1H), 8.57 (d, 1H), 9.06 (dd, 1H), 9.15-9.19 (m, 2H).

7-Chloro-3-ethylsulphonyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline

6-Chloro-3-ethylsulphanyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline(250 mg, 0.59 mmol, mixture with bissulphide) was dissolved indichloromethane (20 ml), and then formic acid (136 mg, 2.95 mmol) andH₂O₂ (402 mg, 4.13 mmol) were added. The mixture was stirred at RT for14 h and washed with sodium thiosulphate solution. The organic phase wasremoved, dried over Na₂SO₄ and concentrated. The solids were trituratedwith MeCN, filtered off and dried under reduced pressure, giving thetitle compound as a clean product.

(log P (neutral): 2.63; MH⁺: 455; ¹H-NMR (400 MHz, CDCl₃): δ 9.05 (s,1H), 8.79 (s, 1H), 8.57 (s, 1H), 8.23 (dd, 1H), 8.14 (d, 1H), 8.12 (d,1H), 4.11 (s, 3H), 3.26 (q, 2H), 1.34 (t, 3H).

3,6-Bis(ethylsulphonyl)-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline

3,6-Bis(ethylsulphanyl)-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline(25 mg, 0.05 mmol) was dissolved in dichloromethane (5 ml), and thenformic acid (13 mg, 0.27 mmol) and H₂O₂ (38 mg, 0.39 mmol) were added.The mixture was stirred at RT for 14 h and washed with sodiumthiosulphate solution. The organic phase was removed, dried over Na₂SO₄and concentrated, giving the title compound as a clean product.

(log P (neutral): 2.58; MH⁺: 513; ¹H-NMR (400 MHz, CDCl₃): δ 9.25 (s,1H), 9.05 (s, 1H), 8.79 (d, 1H), 8.44 (m, 1H), 8.42 (m, 1H), 8.15 (s,1H), 4.00 (s, 3H), 3.91 (q, 2H), 3.29 (q, 2H), 1.42 (t, 3H), 1.38 (t,3H).

6-Chloro-3-ethylsulphanyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline&3,6-bis(ethylsulphanyl)-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline

3,6-Dichloro-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline(0.20 g, 0.50 mmol) was dissolved in DMF (5 ml), and sodiumethylmercaptan (0.169 g, 2.01 mmol) was added. The reaction mixture wasstirred at RT for 14 h, diluted with cyclohexane/ethyl acetate andfiltered. The filtrate was concentrated. The column chromatographypurification of the raw material via preparative HPLC with an MeCN/watergradient as eluent gave the two title compounds as a mixture, which wasconverted further without further purification.

(log P (neutral): 3.99; MH⁺: 423.

(log P (neutral): 4.35; MH⁺: 423.

3,6-Dichloro-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]quinoline(V-4)

3,6-Dichloroquinoline-2-carboxylic acid (1.00 g, 4.13 mmol),N3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (0.61 g, 3.17 mmol)and EDCI*HCl (0.61 g, 3.17 mmol) were dissolved in pyridine (20 ml),p-toluenesulphonic acid (0.60 g, 3.17 mmol) was added and then themixture was stirred at 120° C. for 9 h. After cooling to RT,acetonitrile was added and the suspension obtained was filtered. Thefiltrate was concentrated and the residue was freed of salts by columnchromatography purification with a CH₂Cl₂/MeOH gradient as eluent. Thecrude product obtained was converted further without furtherpurification.

(log P (neutral): 3.53; MH⁺: 397; ¹H-NMR (400 MHz, DMSO-d₆): δ 9.31 (s,1H), 8.91 (s, 1H), 8.34 (s, 1H), 8.29 (d, 1H), 8.20 (d, 1H), 7.95 (dd,1H), 4.03 (s, 3H).

3,6-Dichloroquinoline-2-carboxylic acid (III-2)

A solution of NaClO₂ (6.02 g, 66.7 mmol) and NaH₂PO₄ (8.00 g, 66.7 mmol)in water (25 ml) was added at 0° C. to a solution of3,6-dichloroquinoline-2-carbaldehyde (3.00 g, 13.33 mmol) in t-BuOH (30ml). The mixture was warmed up gradually to RT and stirred at thistemperature for 3 h. After adding water, the product was extracted withdichloromethane. The combined organic phases were washed with saturatedaqueous NaHSO₃ solution and saturated aqueous NaCl solution, dried overNa₂SO₄ and concentrated. The crude product was converted further withoutfurther purification.

MH⁺: 240; ¹H-NMR (400 MHz, DMSO-d₆): δ 7.86-7.89 (dd, J=2.4 & 9.04 Hz,1H), 8.09-8.11 (d, J=9.08 Hz, 1H), 8.17 (d, J=2.36 Hz, 1H), 8.71 (s,1H), 14.26 (brs, 1H).

3,6-Dichloroquinoline-2-carbaldehyde

To a solution of 3,6-dichloro-2-methylquinoline (3.00 g, 14.2 mmol) in1,4-dioxane (30 ml) was added SeO₂ (4.73 g, 42.7 mmol). The mixtureobtained was refluxed for 3 h and then concentrated to dryness.

The crude product was taken up with water. The white solid thatprecipitated out was filtered off, washed with hexane and dried underreduced pressure.

MH⁺: 226; ¹H-NMR (400 MHz, CDCl₃): δ 7.72-7.75 (dd, J=2.28 & 9.0 Hz,1H), 7.80-7.81 (d, J=2.2 Hz, 1H), 8.17-8.19 (d, J=9.24 Hz, 1H), 8.2 (s,1H), 10.37 (s, 1H).

3,6-Dichloro-2-methylquinoline

To a solution of 5-chloro-2-methyl-1H-indole (5.00 g, 30.3 mmol) andTEBAC (0.60 g, 0.300 mmol) in CHCl₃ (150 ml) was added, at 0° C., NaOHin water. The mixture was stirred at 0° C. for 3 h and then at RT for 14h. The reaction mixture was then added gradually to ice-water andextracted with chloroform. The organic phase was washed with water,dried over Na₂SO₄ and concentrated on a rotary evaporator. The residuewas purified by column chromatography purification with a hexane/ethylacetate gradient as eluent.

MH⁺: 212; ¹H-NMR (400 MHz, CDCl₃): δ 2.78 (s, 3H), 7.58-7.61 (dd, J=2.32& 9.0 Hz, 1H), 7.68-7.69 (d, J=2.28 Hz, 1H), 7.91-7.94 (d, J=9.0 Hz,1H), 8.01 (s, 1H).

3,7-Dichloroquinoline-2-carboxylic acid (III-3)

A solution of NaClO₂ (6.02 g, 66.7 mmol) and NaH₂PO₄ (8.00 g, 66.7 mmol)in water (25 ml) was added at 0° C. to a solution of3,7-dichloroquinoline-2-carbaldehyde (3.00 g, 13.33 mmol) in t-BuOH (30ml). The mixture was warmed up gradually to RT and stirred at thistemperature for 3 h. After adding water, the product was extracted withdichloromethane. The combined organic phases were washed with saturatedaqueous NaHCO₃ solution and saturated aqueous NaCl solution, dried overNa₂SO₄ and concentrated. The crude product was converted further withoutfurther purification.

MH⁺: 241; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 14.29 (br, 1H), 8.81 (s, 1H),8.18 (d, 1H), 8.08 (d, 1H), 7.79 (dd, 1H).

3,7-Dichloroquinoline-2-carbaldehyde

To a solution of 3,7-dichloro-2-methylquinoline (3.00 g, 14.2 mmol) in1,4-dioxane (30 ml) was added SeO₂ (4.73 g, 42.7 mmol). The mixtureobtained was refluxed for 3 h and then concentrated to dryness. Thecrude product was taken up with water. The white solid that precipitatedout was filtered off, washed with hexane and dried under reducedpressure.

MH⁺: 226; ¹H-NMR (400 MHz, CDCl₃): δ 7.64-7.67 (dd, J=1.96 & 8.76 Hz,1H), 7.76-7.78 (d, J=8.84 Hz, 1H), 8.24-8.25 (d, J=1.92 Hz, 1H), 8.26(s, 1H), 10.36 (s, 1H).

3,7-Dichloro-2-methylquinoline

To a solution of 6-chloro-2-methyl-1H-indole (5.00 g, 30.3 mmol) andTEBAC (0.60 g, 0.300 mmol) in CHCl₃ (150 ml) was added, at 0° C., NaOHin water. The mixture was stirred at 0° C. for 3 h and then at RT for 14h. The reaction mixture was then added gradually to ice-water andextracted with chloroform. The organic phase was washed with water,dried over Na₂SO₄ and concentrated on a rotary evaporator. The residuewas purified by column chromatography purification with a hexane/ethylacetate gradient as eluent.

MH⁺: 214; ¹H-NMR (400 MHz, CDCl₃): δ 2.79 (s, 3H), 7.44-7.47 (dd, J=2.08& 8.72 Hz, 1H), 7.63-7.65 (d, J=8.72 Hz, 1H), 7.99-8.00 (d, J=1.92 Hz,1H), 8.07 (s, 1H).

6-Chloro-2-methyl-1H-indole

To a solution of 1-(4-chloro-2-nitrophenyl)propan-2-one (10.0 g, 46.9mmol) in EtOH/H₂O (1:1, 50 ml) were added, at 0° C., glacial acetic acid(50 ml) and iron powder (12.4 g, 234.7 mmol). The reaction mixtureobtained was then stirred at 100° C. for 4 h. The mixture wasconcentrated, and the residue was diluted with water and extracted withethyl acetate. The organic phase was washed with water, dried overNa₂SO₄ and then concentrated. The residue was purified by columnchromatography purification with a hexane/ethyl acetate gradient aseluent.

MH⁺: 166; ¹H-NMR (400 MHz, CDCl₃): δ 2.42 (s, 3H), 7.00-7.02 (dd, J=1.84& 8.36 Hz, 1H), 7.25 (s, 1H), 7.37-7.39 (d, J=8.36 Hz, 1H), 7.84 (bs,1H).

1-(4-Chloro-2-nitrophenyl)propan-2-one

Ethyl 2-(2-nitro-4-chlorophenyl)-3-oxobutyrate (28.0 g, 98.2 mmol) wasadded at 0° C. to a solution of glacial acetic acid (60 ml) andsulphuric acid (40 ml). The reaction mixture was then stirred at 100° C.for 8 h. After cooling to RT, the mixture was added gradually toice-water and extracted with ethyl acetate. The combined organic phaseswere washed with water, dried over Na₂SO₄ and freed of the solvent. Thecrude product was purified by column chromatography purification with ahexane/ethyl acetate gradient as eluent.

MH⁺: 212; ¹H-NMR (400 MHz, CDCl₃): δ 2.32 (s, 3H), 4.09 (s, 2H),7.19-7.21 (d, J=9.0 Hz, 1H), 7.54-7.57 (dd, J=2.2 & 8.2 Hz, 1H), 8.11(d, J=2.16 Hz, 1H).

Ethyl 2-(2-nitro-4-chlorophenyl)-3-oxobutyrate

Ethyl acetoacetate (8.16 g, 62.8 mmol) was added at 0° C. to asuspension of Cs₂CO₃ (51.2 g, 157.1 mmol) in DMF (150 ml). After warmingto RT, 1,4-dichloro-2-methylbenzene (10.0 g, 52.4 mmol) was slowly addeddropwise. The reaction mixture obtained was then heated to 80° C. for 4h. For quenching, the mixture was added to ice-water and extracted withethyl acetate. The combined organic phases were washed with water, driedover Na₂SO₄ and concentrated. The residue was converted further withoutfurther purification.

MH⁺: 286.

In analogy to the examples and according to the above-describedpreparation processes, the following compounds of the formula (I) can beobtained:

Ex- am- ple Structure I-1

I-2

I-3

I-4

I-5

I-6

I-7

I-8

I-9

I-10

I-11

I-12

I-13

I-14

I-15

I-16

I-17

I-18

I-19

I-20

I-21

I-22

I-23

I-24

I-25

I-26

I-27

I-28

I-29

I-30

I-31

I-32

I-33

I-34

I-35

I-36

I-37

I-38

I-39

I-40

I-41

I′-42

I′-43

I′-44

I′-45

I-46

I′-47

I′-48

I′-49

I′-50

I′-51

I′-52

I′-53

I′-54

I-55

I-56

I-57

I′-58

I-59

Preparation of N2-methyl-5-(trifluoromethoxy)pyridine-2,3-diamine (II-1)

Step a)

24 g (120 mmol) of 2-chloro-5-(trifluoromethoxy)pyridine, 19.1 g (150mmol) of tert-butyl N-methylcarbamate and 17.5 g (180 mmol) of sodiumtert-butoxide were dissolved in 400 ml of toluene, 2.8 g (3 mmol) oftris(dibenzylideneacetone)dipalladium(0) and 1.73 g (3 mmol) of Xantphoswere added under argon, and the mixture was stirred at 100-105° C. for12 h. Subsequently, the mixture was filtered through Celite and thesolvent was distilled off under reduced pressure.

Step b)

To 100 ml of a sulphuric acid solution cooled to 0° C. were added 30 g(103 mmol) of tert-butylN-methyl-N-[5-(trifluoromethoxy)-2-pyridyl]carbamate and then 10.4 ml(166 mmol) of concentrated nitric acid. The mixture was stirred at 5-10°C. for 2 h and admixed with ice-water. The solution was neutralized withsodium hydroxide and extracted with ethyl acetate. The organic phase wasdried over magnesium sulphate and the solvent was distilled off underreduced pressure. The residue was purified by column chromatographypurification with a chloroform/hexane mixture (1:2) as eluent.

Step c)

A mixture of 10.0 g (42.2 mmol) of tert-butylN-methyl-N-[3-nitro-5-(trifluoromethoxy)-2-pyridyl]carbamate and 0.7 gof palladium/charcoal (10%) was stirred in 250 ml of methanol under ahydrogen atmosphere at room temperature for 2 h. Subsequently, themixture was filtered through Celite and the solvent was distilled offunder reduced pressure. The further purification of the product waseffected by vacuum distillation at 88-90° C. and 0.1 mbar.

¹H NMR (400 MHz, CDCl₃, ppm): δ 7.70 (d, J=0.8 Hz, 1H), 6.75 (d, J=0.8Hz, 1H), 4.20 (br. s., 1H), 3.32 (br. s., 2H), 3.00 (s, 3H). Thismeasurement of the NMR spectrum was effected on a Bruker Avance 3300equipped with a 5 mm broadband liquid probe.

The log P values are measured according to EEC Directive 79/831 AnnexV.A8 by HPLC (high-performance liquid chromatography) on areversed-phase column (C 18). Temperature: 55° C.

The LC-MS determination in the acidic range is effected at pH 2.7 using0.1% aqueous formic acid and acetonitrile (contains 0.1% formic acid) aseluents; linear gradient from 10% acetonitrile to 95% acetonitrile.Called log P (HCOOH) in the table.

LC-MS determination in the neutral range is effected at pH 7.8 with0.001 molar aqueous ammonium hydrogencarbonate solution and acetonitrileas eluents; linear gradient from 10% acetonitrile to 95% acetonitrile.Called log P (neutral) in the table.

Calibration is carried out using unbranched alkan-2-ones (having 3 to 16carbon atoms) with known log P values (log P values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones).

The NMR data of selected examples are listed either in conventional form(8 values, multiplet splitting, number of hydrogen atoms) or as NMR peaklists.

In each case, the solvent in which the NMR spectrum was recorded isstated.

NMR Peak List Method

The NMR data of selected examples are stated in the form of NMR peaklists. For each signal peak, first the δ value in ppm and then thesignal intensity in round brackets are listed. The pairs of δvalue-signal intensity numbers for different signal peaks are listedwith separation from one another by semicolons.

The peak list for one example therefore has the form:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

Calibration of the chemical shift of NMR spectra is accomplished usingtetramethylsilane and/or the chemical shift of the solvent, particularlyin the case of spectra which are measured in DMSO. Therefore, thetetramethylsilane peak may but need not occur in NMR peak lists.

The lists of the NMR peaks are similar to the conventional ¹H-NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds which arelikewise provided by the invention, and/or peaks of impurities.

In the reporting of compound signals within the delta range of solventsand/or water, our lists of NMR peaks show the standard solvent peaks,for example peaks of DMSO in DMSO-D₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in identifyingreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the peak picking in question in conventional NMRinterpretation.

Further details of NMR peak lists can be found in the ResearchDisclosure Database Number 564025.

Example I-1: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.338(4.4); 9.320(3.8);8.518(1.5); 8.498(1.6); 8.328(4.0); 8.300(1.5); 8.278(2.0); 8.172(0.9);8.168(0.9); 8.154(1.2); 8.151(1.6); 8.133(0.8); 8.130(0.8); 7.993(1.0);7.991(1.0); 7.973(1.7); 7.955(0.8); 7.953(0.8); 3.927(16.0); 3.864(1.0);3.846(3.4); 3.827(3.4); 3.809(1.0); 3.321(49.5); 2.672(0.4); 2.525(0.9); 2.512(22.4); 2.507(46.3); 2.503(61.4); 2.498(44.5); 2.494(21.5);2.330(0.4); 2.074(1.7); 1.252(3.6); 1.234(8.1); 1.215(3.5); 0.000(1.7)Example I-2: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.289(4.1); 8.816(0.4);8.584(4.4); 8.317(4.4); 8.290(0.7); 8.135(0.5); 8.107(3.4); 8.085(3.9);7.953(0.4); 7.838(0.8); 7.823(1.4); 7.820(1.7); 7.799(1.3); 7.776(1.3);7.774(1.3); 7.756(1.6); 7.736(0.7); 7.572(0.3); 6.839(0.4); 4.029(16.0);3.385(0.8); 3.333(91.2); 3.324(82.2); 3.151(1.2); 3.133(3.8);3.115(3.9); 3.096(1.3); 2.891(2.9); 2.879(0.8); 2.811(0.6); 2.799(0.6);2.732(2.0); 2.671(0.7); 2.667(0.6); 2.507(91.1); 2.502(120.9);2.498(95.2); 2.329(0.7); 1.316(0.5); 1.310(0.3); 1.298(0.9); 1.285(4.1);1.267(8.5); 1.249(4.0); 1.169(0.3); 0.000(1.3) Example I-3: ¹H-NMR(400.0MHz, d₆-DMSO): δ = 9.382(0.4); 9.321(4.0); 8.471(1.3); 8.466(0.9);8.458(1.4); 8.454(1.0); 8.447(1.5); 8.439(0.3); 8.401(1.2); 8.395(1.0);8.390(1.8); 8.382(1.3); 8.377(1.8); 8.370(0.6); 8.333(4.2); 8.265(0.6);8.252(2.6); 8.248(1.9); 8.240(2.2); 8.233(1.6); 8.228(2.3); 8.216(0.4);5.754(0.7); 4.390(1.7); 3.993(16.0); 3.847(1.2); 3.829(4.0); 3.810(4.0);3.792(1.2); 3.317(37.4); 2.676(0.4); 2.671(0.5); 2.667(0.4);2.506(58.3); 2.502(77.1); 2.497(58.9); 2.333(0.4); 2.329(0.5);2.324(0.4); 1.425(0.4); 1.406(0.9); 1.388(0.4); 1.289(4.1); 1.270(8.8);1.252(4.0); 0.000(2.9) Example I-4: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =9.331(3.4); 8.368(3.5); 8.366(3.6); 8.184(1.3); 8.181(1.4); 8.163(1.6);8.161(1.6); 8.086(1.2); 8.084(1.3); 8.065(1.7); 8.063(1.7); 7.980(0.9);7.976(1.0); 7.963(1.2); 7.959(1.6); 7.956(0.8); 7.942(0.9); 7.938(0.9);7.872(1.1); 7.868(1.1); 7.854(0.9); 7.851(1.6); 7.848(1.1); 7.834(0.7);7.830(0.7); 4.178(16.0); 3.327(2.2); 3.317(49.6); 3.309(4.9);3.290(4.0); 3.272(1.3); 2.671(0.4); 2.511(24.5); 2.507(48.6);2.502(65.4); 2.498(49.8); 2.493(25.2); 2.472(0.5); 2.329(0.4);1.398(0.4); 1.384(4.1); 1.366(8.9); 1.347(4.0); 0.146(0.3); 0.008(3.7);0.000(82.5); −0.008(3.5); −0.150(0.4) Example I-5: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.342(4.1); 8.924(2.2); 8.921(2.2); 8.712(2.2);8.708(2.2); 8.518(1.4); 8.498(1.5); 8.304(1.3); 8.283(1.8); 8.172(0.9);8.168(0.9); 8.154(1.1); 8.151(1.5); 8.147(0.8); 8.133(0.9); 8.129(0.8);7.992(1.0); 7.989(1.0); 7.971(1.6); 7.969(1.1); 7.954(0.8); 7.951(0.8);5.756(0.9); 3.903(0.9); 3.884(3.2); 3.866(3.2); 3.847(1.0); 3.833(16.0);3.323(80.9); 2.676(0.3); 2.672(0.4); 2.667(0.3); 2.525(1.0);2.511(25.5); 2.507(54.0); 2.502(75.3); 2.498(55.4); 2.493(25.9);2.329(0.5); 1.265(3.3); 1.246(7.6); 1.228(3.3); 0.008(0.5); 0.000(17.4);−0.009(0.6) Example I-6: ¹H-NMR(400.0 MHz, CDCl₃): δ = 9.245(4.5);9.045(3.7); 8.795(2.5); 8.791(2.5); 8.464(1.0); 8.442(3.3); 8.426(2.5);8.421(2.3); 8.403(0.8); 8.399(0.8); 8.148(3.9); 7.265(14.1); 5.301(0.7);3.996(16.0); 3.939(1.0); 3.921(3.5); 3.902(3.6); 3.884(1.1); 3.319(1.1);3.300(3.6); 3.281(3.7); 3.263(1.2); 1.624(11.0); 1.440(3.6); 1.421(7.7);1.402(6.1); 1.382(8.0); 1.364(3.6); 1.255(0.9); 0.000(0.5) Example I-7:¹H-NMR(601.6 MHz, CDCl₃): δ = 9.014(3.6); 8.996(4.2); 8.211(2.0);8.197(2.3); 8.128(6.8); 7.970(2.0); 7.966(1.5); 7.955(1.8); 7.952(1.3);7.265(1.8); 7.261(4.8); 5.302(0.6); 5.298(1.5); 3.950(16.0); 3.872(1.2);3.859(3.8); 3.847(3.8); 3.835(1.2); 1.565(3.0); 1.401(3.9); 1.388(8.0);1.376(3.7); 1.257(0.4); 0.004(1.9); 0.000(5.0) Example I-8: ¹H-NMR(601.6MHz, CDCl₃): δ = 9.053(3.3); 8.793(2.3); 8.792(2.5); 8.790(2.4);8.565(3.7); 8.227(3.4); 8.226(3.4); 8.153(1.0); 8.150(1.1); 8.138(2.0);8.136(2.1); 8.108(2.8); 8.094(1.6); 7.265(6.5); 5.299(1.2); 4.114(16.0);4.011(0.4); 3.938(0.4); 3.279(1.1); 3.267(3.6); 3.254(3.6); 3.242(1.2);1.612(2.0); 1.370(3.7); 1.357(7.9); 1.345(3.7); 1.322(0.5); 1.256(0.4);0.000(4.7) Example I-9: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.340(4.1);8.840(2.5); 8.685(1.7); 8.663(2.1); 8.490(1.7); 8.485(1.6); 8.468(1.3);8.463(1.4); 8.357(4.4); 8.315(0.5); 4.096(0.4); 4.025(16.0); 3.896(1.1);3.877(3.9); 3.859(3.9); 3.840(1.2); 3.320(70.9); 2.676(1.0); 2.671(1.4);2.666(1.0); 2.524(3.5); 2.510(79.2); 2.506(167.8); 2.502(236.0);2.497(178.5); 2.333(1.0); 2.328(1.4); 2.324(1.0); 1.305(4.1);1.287(8.9); 1.268(4.0); 1.235(0.9); 0.146(0.7); 0.008(5.0);0.000(162.7); −0.008(6.4); −0.150(0.7) Example I-10: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.344(8.5); 8.520(1.5); 8.501(1.6); 8.360(4.4);8.358(4.3); 8.297(1.5); 8.276(2.0); 8.173(0.9); 8.170(0.9); 8.156(1.2);8.152(1.6); 8.135(0.9); 8.131(0.9); 7.996(1.1); 7.993(1.1); 7.975(1.7);7.958(0.8); 7.955(0.8); 3.929(16.0); 3.873(1.0); 3.854(3.4); 3.836(3.5);3.817(1.0); 3.319(42.6); 2.675(0.9); 2.671 (1.2); 2.666(0.9);2.524(2.9); 2.519(4.5); 2.511(74.4); 2.506(154.2); 2.502(204.0);2.497(145.1); 2.493(69.5); 2.333(0.9); 2.328(1.2); 2.324(0.9);1.398(8.1); 1.251(3.6); 1.232(8.1); 1.214(3.5); 0.146(0.3); 0.008(2.3);0.000(74.8); −0.008(2.7); −0.150(0.3) Example I-11: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.701(6.1); 9.234(8.6); 8.736(9.1); 8.412(3.2);8.395(8.0); 8.206(2.9); 8.184(4.0); 8.084(1.9); 8.081(1.9); 8.067(2.4);8.064(3.2); 8.046(1.7); 8.043(1.6); 7.871(2.1); 7.869(2.1); 7.851(3.4);7.833(1.7); 7.831(1.6); 5.758(0.9); 4.174(1.9); 4.156(6.5); 4.137(6.5);4.119(2.0); 4.099(0.5); 4.085(0.4); 3.322(51.5); 3.176(2.4); 3.163(2.3);2.676(0.6); 2.672(0.8); 2.667(0.6); 2.525(2.1); 2.507(108.3);2.503(142.1); 2.498(103.3); 2.334(0.6); 2.329(0.8); 2.325(0.6);1.305(7.2); 1.286(16.0); 1.268(7.1); 1.259(1.4); 1.241(1.0); 1.233(1.0);0.880(0.6); 0.008(0.9); 0.000(29.2); −0.009(1.2) Example I-12:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.308(4.8); 8.502(1.7); 8.482(1.8);8.282(1.6); 8.261(2.2); 8.151(4.0); 8.134(1.7); 8.116(0.8); 8.113(0.9);7.984(1.9); 7.970(1.4); 7.963(2 4); 7.952(1.8); 7.932(0.9); 7.753(1.7);7.732(1.4); 3.926(1.0); 3.908(3.5); 3.889(3.5); 3.871(1.1); 3.817(16.0);3.320(31.9); 2.670(1.3); 2.666(1.1); 2.523(2.9); 2.506 (167.3);2.501(228.6); 2.497(175.1); 2.332(1.0); 2.328(1.3); 2.324(1.1);1.397(2.8); 1.253(3.6); 1.235(8.0); 1.217(3.6); 0.146(0.4); 0.008(2.2);0.000(74.0); −0.150(0.4) Example I-13: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =9.396(8.7); 9.044(6.3); 9.032(5.5); 8.522(3.1); 8.502(3.3); 8.360(3.1);8.339(4.0); 8.203(1.8); 8.200(1.8); 8.185(2.4); 8.182(3.2); 8.164(1.8);8.161(1.7); 8.025(2.1); 8.023(2.1); 8.005(3.4); 7.987(1.7); 3.962(2.1);3.943(7.0); 3.925(7.1); 3.906(2.2); 3.321(41.5); 3.151(0.8); 2.676(0.8);2.672(1.1); 2.667(0.8); 2.525(2.7); 2.507(143.3); 2.503(183.1);2.498(133.7); 2.334(0.8); 2.329(1.1); 2.325(0.8); 1.990(0.7);1.397(7.6); 1.340(7.4); 1.322(16.0); 1.303(7.1); 1.175(0.4); 0.000(2.0)Example I-14: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.366(8.9); 8.510(3.2);8.490(3.4); 8.406(5.6); 8.403(5.7); 8.329(3.1); 8.308(4.1); 8.183(1.9);8.180(1.9); 8.165(2.6); 8.162(3.6); 8.157(5.8); 8.144(2.1); 8.141(2.1);8.135(6.2); 8.004(2.2); 7.984(3.5); 7.966(1.8); 7.950(3.3); 7.946(3.2);7.929(2.7); 7.925(2.7); 4.013(2.0); 3.995(6.9); 3.976(7.0); 3.958(2.1);3.322(22.1); 2.677(0.5); 2.673(0.6); 2.508(83.7); 2.504(107.7);2.499(78.2); 2.330(0.6); 2.326(0.5); 1.990(0.5); 1.397(15.1);1.336(7.3); 1.317(16.0); 1.299(7.1); 0.146(0.4); 0.008(3.0);0.000(78.2); −0.008(3.8); −0.149(0.4) Example 1-15: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 13.544(4.7); 9.270(10.1); 8.445(4.0); 8.424(4.2);8.256(3.8); 8.235(5.0); 8.121(2.3); 8.103(3.7); 8.082(2.0); 7.907(2.6);7.888(4.0); 7.869(2.2); 7.800(1.0); 7.632(1.0); 4.342(2.2); 4.324(7.0);4.305(7.1); 4.287(2.3); 3.319(42.7); 2.671(2.2); 2.502(366.5);2.329(2.1); 1.397(2.2); 1.322(7.5); 1.304(16.0); 1.286(7.5); 1.233(0.5);0.000(53.2) Example I-16: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.280(4.8);8.483(1.6); 8.462(1.8); 8.265(16); 8.244(2.2); 8.139(1.0); 8.137(1.0);8.119(1.8); 8.101(1.0); 8.098(0.9); 7.952(1.2); 7.933(1.8); 7.913(1.2);7.906(5.8); 7.804(6.0); 4.548(0.7); 3.935(1.0); 3.917(3.4); 3.898(3.5);3.880(1.1); 3.763(16.0); 3.320(48.0); 2.675(0.7); 2.671(0.9);2.506(120.5); 2.502(157.3); 2.497(116.2); 2.333(0.7); 2.328(0.9);2.324(0.7); 2.117(2.2); 1.304(0.4); 1.244(4.1); 1.226(8.4); 1.207(3.7);1.140(4.9); 0.008(0.8); 0.000(16.0) Example I-17: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.370(8.8); 8.513(3.1); 8.493(3.3); 8.435(5.2);8.339(3.1); 8.318(4.0); 8.216(3.6); 8.194(4.5); 8.186(2.1); 8.183(2.0);8.169(2.4); 8.165(3.2); 8.148(1.8); 8.144(1.7); 8.007(2.1); 8.005(2.2);7.987(6.2); 7.967(4.0); 4.013(2.0); 3.995(6.9); 3.976(7.0); 3.958(2.2);3.323(27.9); 2.677(0.5); 2.672(0.6); 2.668(0.5); 2.508(85.4);2.503(111.3); 2.499(81.1); 2.334(0.5); 2.330(0.6); 1.990(0.6);1.397(4.8); 1.338(7.3); 1.320(16.0); 1.301(7.2); 1.175(0.3); 0.000(2.1)Example I-18: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.396(8.7); 8.872(5.2);8.868(5.4); 8.524(3.1); 8.504(3.4); 8.460(4.0); 8.438(6.5); 8.371(3.4);8.367(3.4); 8.345(5.2); 8.323(4.1); 8.198(1.8); 8.195(1.8); 8.177(3.2);8.159(1.8); 8.156(1.9); 8.022(2.2); 8.002(3.4); 7.984(1.8); 4.038(0.7);4.021(2.7); 4.003(7.1); 3.984(6.9); 3.965(2.1); 3.319(112.3); 2.675(1.5); 2.671(2.1); 2.667(1.6); 2.507(270.1); 2.502(351.4); 2.498(258.1);2.333(1.5); 2.329(2.0); 1.989(2.5); 1.344(7.3); 1.325(16.0); 1.307(7.2);1.241(1.7); 1.193(0.7); 1.175(1.4); 1.157(0.7); 0.146(1.6); 0.008(18.0);0.000(369.9); −0.008(19.6); −0.150(1.7) Example I-19: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.377(9.2); 8.555(6.3); 8.517(3.5); 8.496(3.7);8.344(5.2); 8.336(3.8); 8.323(6.5); 8.315(5.1); 8.189(2.0); 8.187(2.0);8.169(3.5); 8.151(1.9); 8.148(1.9); 8.126(3.5); 8.105(2.9); 8.009(2.4);7.991(3.7); 7.973(1.9); 4.038(0.8); 4.019(2.7); 4.001(7.2); 3.982(7.2);3.964(2.3); 3.320(127.4); 2.671(1.9); 2.502 (328.7); 2.498(252.0);2.329(2.0); 1.989(2.9); 1.341(7.4); 1.322(16.0); 1.304(7.3); 1.193(0.8);1.175(1.6); 1.158(0.9); 0.146(1.5); 0.000(314.0); −0.150(1.5) ExampleI-20: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.347(4.5); 8.856(2.4);8.851(2.5); 8.671(2.5); 8.667(2.4); 8.520(1.5); 8.501(1.6); 8.299(1.5);8.278(2.0); 8.172(0.9); 8.168(0.9); 8.154(1.2); 8.151(1.6); 8.133(0.9);8.130(0.8); 7.990(1.1); 7.972(1.7); 7.955(0.9); 4.418(0.4); 3.912(0.9);3.894(3.4); 3.876(3.5); 3.857(1.2); 3.844(16.0); 3.320(26.1); 2.676(0.6); 2.671(0.7); 2.667(0.6); 2.525(1.9); 2.511(47.8); 2.507(97.0);2.502(127.6); 2.498(91.3); 2.494(44.2); 2.333(0.5); 2.329(0.8);1.264(3.5); 1.246(8.1); 1.235(2.1); 1.227(3.8); 0.146(0.6); 0.008(4.6);0.000(125.9); −0.008(5.3); −0.150(0.6) Example I-21: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.306(4.5); 8.500(1.6); 8.480(1.7); 8.270(1.5);8.249(2.1); 8.153(3.5); 8.131(1.7); 8.113(0.9); 8.110(0.8); 7.969(1.1);7.967(1.1); 7.949(1.7); 7.927(2.7); 7.906(2.8); 7.735(1.6); 7.732(1.6);7.714(1.4); 7.710(1.4); 3.930(0.9); 3.911(3.2); 3.893(3.3); 3.875(1.0);3.803(15.0); 3.325(91.4); 2.671(0.5); 2.667 (0.4); 2.507(72.7);2.502(93.6); 2.498(68.1); 2.329(0.5); 1.398(16.0); 1.253(3.4);1.234(7.8); 1.216(3.4); 0.146(0.4); 0.008(3.7); 0.000(79.4);−0.008(3.7); −0.150(0.4) Example I-22: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =9.389(4.7); 8.807(6.3); 8.542(2.0); 8.523(1.9); 8.329(1.7); 8.308(2.3);8.197(1.2); 8.177(1.9); 8.159(1.0); 8.023(1.4); 8.003(2.0); 7.983(1.0);5.756(0.5); 4.007(16.0); 3.833(1.2); 3.814(3.6); 3.796(3.6); 3.778(1.1);3.539(0.4); 3.321(145.9); 3.256(0.6); 2.671(1.6); 2.506(238.8);2.502(294.2); 2.497(210.6); 2.329(1.6); 1.264(4.1); 1.246(8.7);1.227(4.4); 1.207(0.7); 1.189(1.0); 1.182(0.4); 1.173(0.9); 1.155(0.5);0.854(0.3); 0.146(0.5); 0.000(101.4); −0.149(0.5) Example I-23:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.320(5.2); 8.508(1.9); 8.488(2.1);8.338(3.8); 8.276(1.8); 8.254(2.5); 8.157(1.1); 8.138(1.9); 8.117(3.4);8.096(3.1); 7.976(1.3); 7.957(2.0); 7.938(1.1); 7.921(2.0); 7.900(1.7);3.927(1.1); 3.908(3.5); 3.890(3.6); 3.871(1.3); 3.844(16.0);3.321(40.5); 2.672(0.6); 2.502(109.7); 2.329(0.6); 1.397(4.1);1.257(3.8); 1.238(8.3); 1.220(3.8); 0.000(48.0) Example I-24:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.340(4.6); 8.561(3.1); 8.518(1.7);8.497(1.8); 8.285(1.6); 8.263(2.2); 8.225(2.1); 8.203(3.1); 8.165(1.0);8.147(1.7); 8.124(2.2); 8.102(1.2); 8.098(1.2); 7.987(1.1); 7.969(1.8);7.951(0.9); 4.056(0.4); 4.039(1.1); 4.021(1.1); 4.003(0.4); 3.908(1.1);3.884(16.0); 3.871(3.8); 3.853(1.1); 3.322(25.6); 2.672 (0.5);2.507(61.5); 2.503(79.8); 2.498(59.6); 2.329(0.4); 1.989(4.6);1.397(2.1); 1.260(3.5); 1.242(7.7); 1.224(3.5); 1.193(1.3); 1.175(2.4);1.158(1.2); 0.000(29.1) Example I-25: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =8.896(2.3); 8.893(2.3); 8.700(2.5); 8.697(2.3); 8.569(4.0); 8.111(1.6);8.096(1.6); 8.091(1.8); 8.080(1.6); 7.835(0.7); 7.832(0.7); 7.818(1.2);7.814(1.5); 7.797(1.1); 7.793(1.0); 7.769(1.2); 7.766(1.2); 7.749(1.5);7.732(0.7); 3.982(16.0); 3.319(54.7); 3.159(1.1); 3.140(3.5);3.122(3.5); 3.104(1.1); 2.672 (0.5); 2.507(51.6); 2.503(69.7);2.498(51.9); 2.330(0.4); 1.397(2.4); 1.299(3.8); 1.280(8.0); 1.262(3.7);0.008(1.8); 0.000(40.5); −0.008(1.7) Example I-26: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.080(4.2); 8.356(1.5); 8.337(1.6); 8.305(1.5);8.284(1.8); 8.203(2.6); 8.028(1.9); 8.005(3.0); 7.987(0.9); 7.984(0.9);7.860(1.0); 7.857(1.0); 7.840(1.7); 7.822(0.8); 7.820(0.8); 7.768(1.4);7.765(1.4); 7.746(1.2); 7.743(1.2); 4.383(16.0); 3.643(0.9); 3.624(1.0);3.610(1.1); 3.591(1.0); 3.320(13.3); 3.031 (1.0); 3.013(1.1);2.998(1.0); 2.980(1.0); 2.676(0.4); 2.671(0.6); 2.667(0.4); 2.524(1.4);2.511(34.4); 2.507(70.4); 2.502(92.9); 2.498(67.2); 2.494(32.9);2.333(0.4); 2.329(0.5); 2.325(0.4); 1.989(0.4); 1.313(3.7); 1.295(8.0);1.276(3.6); 1.231(0.4); 0.146(0.5); 0.008(3.3); 0.000(96.4);−0.008(4.1); −0.150(0.5) Example I-27: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =9.013(3.9); 9.008(5.0); 8.972(4.4); 8.968(3.8); 8.555(7.2); 8.185(2.9);8.164(3.2); 8.100(2.5); 8.081(2.8); 8.079(2.8); 7.850(1.2); 7.846(1.4);7.832(2.2); 7.829(2.9); 7.825(1.5); 7.812(2.1); 7.808(2.0); 7.785(2.1);7.782(2.5); 7.765(2.9); 7.762(2.4); 7.748(1.2); 7.745(1.3); 3.321(34.2);3.248(1.9); 3.230(6.5); 3.212(6.6); 3.193(2.1); 3.078(1.1); 2.677(0.5);2.672(0.8); 2.668(0.6); 2.525(1.7); 2.521.(2.6); 2.512(43.1);2.508(92.6); 2.503(125.7); 2.499(91.2); 2.494(44.3); 2.334(0.5);2.330(0.7); 2.325(0.5); 1.402(7.3); 1.384(16.0); 1.365(7.1); 1.350(0.4);0.008(0.3); 0.000(11.2); −0.008(0.4) Example I-28: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.097(9.4); 9.036(4.7); 9.032(5.7); 8.994(5.2);8.411(3.4); 8.388(5.7); 8.365(4.1); 8.073(1.8); 8.054(3.2); 8.036(1.9);7.922(2.4); 7.903(3.4); 7.884(1.8); 3.555(0.5); 3.536(1.8); 3.518(2.1);3.502(2.3); 3.484(2.1); 3.465(0.6); 3.319(76.6); 3.020(0.6); 3.001(2.1);2.983(2.3); 2.968(2.2); 2.949(1.9); 2.931(0.6); 2.671(2.4);2.506(320.5); 2.502(411.7); 2.498(298.4); 2.328(2.4); 1.989(0.5);1.397(0.8); 1.263(7.5); 1.245(16.0); 1.226(7.3); 1.175(0.4); 0.000(4.5)Example I-29: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 8.537(7.6); 8.408(4.8);8.405(4.9); 8.154(3.2); 8.142(5.2); 8.133(3.7); 8.120(6.0); 8.092(2.8);8.073(3.1); 7.915(3.1); 7.911(3.1); 7.894(2.6); 7.890(2.6); 7.834(1.3);7.830(1.5); 7.817(2.5); 7.813(3.0); 7.796(2.2); 7.792(2.0); 7.769(2.3);7.767(2.4); 7.749(3.1); 7.732(1.3); 7.729(1.3); 3.321(49.4); 3.236(2.0);3.218(6.7); 3.199(6.8); 3.181(2.2); 2.676(1.0); 2.672(1.3); 2.667(1.0);2.525(2.9); 2.507(128.8); 2.503(169.0); 2.498(122.4); 2.334(1.0);2.329(1.3); 2.325(1.0); 1.393(7.8); 1.375(16.0); 1.357(7.2); 0.000(4.8)Example I-30: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.068(8.7); 8.425(5.6);8.421(5.7); 8.393(3.1); 8.374(3.3); 8.345(3.4); 8.324(3.8); 8.185(5.1);8.164(6.0); 8.053(1.8); 8.032(3.2); 8.014(1.8); 8.011(1.9); 7.936(3.3);7.932(3.0); 7.915(2.7); 7.911(2.6); 7.900(2.2); 7.880(3.3); 7.862(1.8);3.578(0.5); 3.559(1.9); 3.540(2.1); 3.525(2.3); 3.506(2.0); 3.487(0.7);3.318(145.3); 3.027(0.7); 3.008(2.2); 2.990(2.3); 2.975(2.3);2.956(1.9); 2.938(0.6); 2.675(3.6); 2.670(4.9); 2.666(3.6); 2.608(0.5);2.524(13.1); 2.506(637.5); 2.502(820.8); 2.497(582.4); 2.333(3.4);2.328(4.6); 2.324(3.5); 1.988(0.4); 1.398(3.3); 1.266(7.4); 1.248(16.0);1.229(7.3); 1.167(0.3); 0.146(2.5); 0.008(20.7); 0.000(548.6);−0.008(20.5); −0.149(2.3) Example I-31: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =13.309(3.9); 8.373(8.3); 8.084(3.5); 8.063(4.0); 8.032(3.2); 8.012(3.5);7.844(2.7); 7.784(1.7); 7.781(1.8); 7.764(3.3); 7.747(2.1); 7.743(2.0);7.680(2.4); 7.661(3.4); 7.643(1.6); 7.558(2.7); 3.321(90.4); 3.172(2.1);3.153(6.8); 3.135(7.0); 3.117(2.2); 2.675(1.5); 2.671(2.0); 2.666(1.5);2.524(4.7); 2.506 (259.4); 2.502(340.0); 2.498(245.8); 2.333(1.5);2.329(2.0); 2.324(1.5); 1.404(7.5); 1.386(16.0); 1.368(7.2); 1.312(0.3);0.146(0.7); 0.008(5.3); 0.000(154.9); −0.008(6.2); −0.150(0.7) ExampleI-32: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 8.541(8.1); 8.431(5.4);8.196(3.8); 8.174(4.6); 8.158(3.4); 8.137(3.7); 8.094(3.0); 8.075(3.3);7.946(3.0); 7.943(3.0); 7.925(2.6); 7.921(2.6); 7.836(1.4); 7.833(1.5);7.819(2.6); 7.816(3.1); 7.798(2.3); 7.795(2.1); 7.771(2.4); 7.769(2.5);7.751(3.3); 7.734(1.4); 3.322(44.3); 3.237(2.1); 3.218(7.0); 3.200(7.1);3.182(2.3); 2.677(0.8); 2.672(1.0); 2.668(0.8); 2.508(124.2);2.503(160.8); 2.499(118.4); 2.330(0.9); 2.325(0.7); 1.393(7.7);1.374(16.0); 1.356(7.3); 0.000(17.4) Example I-33: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.073(6.9); 8.444(4.4); 8.394(2.6); 8.374(2.8);8.345(2.7); 8.323(3.1); 8.238(2.9); 8.216(3.4); 8.051(1.4); 8.033(2.4);8.013(1.5); 7.964(2.4); 7.942(2.1); 7.900(1.8); 7.881(2.6); 7.862(1.4);3.575(0.4); 3.557(1.3); 3.538(1.6); 3.523(1.6); 3.504(1.5); 3.486(0.5);3.321(52.8); 3.021(0.4); 3.003(1.5); 2.984(1.8); 2.969(1.6); 2.951(1.4);2.933(0.4); 2.671(1.0); 2.502(172.9); 2.329(1.0); 1.397(16.0);1.276(5.4); 1.258(11.4); 1.240(5.3); 0.000(2.6) Example I-34:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 8.526(4.4); 8.316(0.4); 8.159(3.3);8.081(2.7); 8.060(3.1); 7.900(2.4); 7.878(2.9); 7.815(0.8); 7.796(1.6);7.778(1.2); 7.750(1.4); 7.729(1.8); 7.713(2.5); 7.693(1.5); 3.906(16.0);3.322(207.8); 3.143(1.2); 3.125(3.8); 3.107(3.9); 3.088(1.3);2.671(1.8); 2.506(247.9); 2.502(313.4); 2.498(227.1); 2.328(1.7);2.074(0.6); 1.292(4.1); 1.274(8.7); 1.255(3.9); 0.146(1.2); 0.008(12.9);0.000(260.3); −0.149(1.2) Example I-35: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =9.317(3.9); 8.590(4.2); 8.348(4.0); 8.346(4.1); 8.109(3.0); 8086(3.7);7.842(0.7); 7.839(0.7); 7.825(1.3); 7.822(1.4); 7.804(1.0); 7.801(1.1);7.779(1.2); 7.776(1.2); 7.758(1.4); 7.741(0.6); 7.739(0.7); 4.032(16.0);3.157(1.1); 3.138(3.7); 3.120(3.8); 3.102(1.2); 2.513(14.0);2.509(28.3); 2.504(37.2); 2.500(27.4); 1.396(8.0); 1.288(4.1);1.269(8.7); 1.251(4.0); 1.197(0.4); 0.000(3.6) Example I-36:¹H-NMR(600.1 MHz, CD3CN): δ = 11.745(0.5); 8.966(6.6); 8.206(2.5);8.192(2.7); 8.191(2.7); 8.163(2.3); 8.161(2.3); 8.149(2.4); 8.148(2.5);7.936(1.6); 7.934(1.5); 7.925(1.9); 7.922(2.9); 7.920(1.5); 7.911(1.6);7.908(1.5); 7.755(1.7); 7.753(1.7); 7.743(1.8); 7.741(3.0); 7.739(1.8);7.730(1.5); 7.728(1.4); 7.579(1.4); 7.483(1.4); 3.575(0.6); 3.562(1.8);3.552(0.8); 3.550(2.0); 3.540(2.1); 3.538(0.8); 3.528(2.0); 3.515(0.6);2.984(0.6); 2.971(2.0); 2.959(2.2); 2.949(2.0); 2.947(0.9); 2.937(1.9);2.925(0.6); 2.130(50.4); 2.058(0.4); 2.054(0.6); 2.050(0.9); 2.046(0.6);1.964(3.8); 1.956(6.9); 1.951(8.6); 1.948(62.4); 1.943(113.2);1.939(164.6); 1.935(112.0); 1.931(56.5); 1.922(1.1); 1.833(0.4);1.828(0.7); 1.824(0.9); 1.820(0.6); 1.816(0.3); 1.451(0.4); 1.340(0.7);1.320(7.8); 1.308(16.0); 1.296(7.6); 1.285(1.1); 1.268(1.8); 0.881(0.4);0.005(0.5); 0.000(16.1); −0.006(0.6) Example I-37: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 8.829(2.3); 8.824(2.4); 8.659(2.4); 8.655(2.3);8.574(4.0); 8.110(1.6); 8.102(1.4); 8.089(1.8); 8.082(1.6); 7.836(0.7);7.833(0.7); 7.819(1.2); 7.815(1.5); 7.798(1.0); 7.794(1.0); 7.772(1.1);7.768(1.2); 7.751(1.5); 7.734(0.7); 7.731(0.6); 3.989(16.0); 3.328(1.2);3.164(1.1); 3.146(3.6); 3.127(3.7); 3.109(1.2); 2.673(0.4); 2.526(0.9);2.512(23.0); 2.508(47.2); 2.504(62.5); 2.499(44.6); 2.495(21.3);2.330(0.3); 1.301(3.9); 1.283(8.3); 1.265(3.8); 1.232(1.7); 0.008(0.4);0.000(12.0); −0.009(0.4) Example I-38: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =8.618(2.6); 8.553(4.3); 8.428(2.5); 8.100(2.0); 8.090(1.9); 8.079(2.3);8.074(2.1); 7.825(0.9); 7.807(1.6); 7.790(1.2); 7.786(1.1); 7.760(1.3);7.742(1.7); 7.724(0.8); 3.951(16.0); 3.814(0.5); 3.323(100.5);3.156(1.2); 3.137(3.7); 3.119(3.8); 3.100(1.3); 2.671(1.3);2.506(182.8); 2.502(229.6); 2.498(173.1); 2.329(1.2); 1.299(4.0);1.281(8.3); 1.263(4.1); 1.235(3.3); 0.854(0.3); 0.146(0.8);0.000(148.6); −0.149(0.7) Example I-39: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =8.532(4.8); 8.427(0.4); 8.150(3.6); 8.089(4.0); 8.068(4.4); 7.958(2.1);7.936(2.5); 7.819(0.9); 7.802(1.9); 7.782(1.4); 7.753(1.6); 7.733(4.3);7.713(2.5); 3.923(16.0); 3.325(15.4); 3.140(1.2); 3.122(3.9);3.104(4.0); 3.085(1.4); 2.805(0.6); 2.794(0.6); 2.671(0.5); 2.502(80.3);2.329(0.5); 1.397(1.5); 1.347(0.4); 1.329(0.7); 1.311(0.4); 1.288(4.2);1.269(8.6); 1.251(4.0); 0.000(9.9) Example I-40: ¹H-NMR(400.0 MHz,CD3CN): δ = 9.101(3.4); 8.922(2.5); 8.916(2.5); 8.287(4.5); 8.180(3.7);8.153(2.5); 8.147(2.4); 4.062(16.0); 3.219(1.2); 3.201(3.7); 3.183(3.8);3.164(1.3); 3.131(1.1); 3.112(3.5); 3.094(3.5); 3.076(1.2); 2.131(29.4);2.129(37.1); 2.113(0.7); 2.107(0.7); 2.100(0.5); 1.971(1.0); 1.963(2.8);1.952(40.0); 1.945(73.2); 1.939(97.8); 1.933(67.1); 1.927(34.0);1.774(0.4); 1.768(0.6); 1.762(0.4); 1.438(4.0); 1.420(8.0); 1.401(3.9);1.361(3.9); 1.342(7.9); 1.324(3.7); 1.204(0.4); 0.000(1.5) Example I-41:¹H-NMR(400.0 MHz, CD3CN): δ = 9.656(2.7); 9.649(2.7); 9.429(5.4);9.267(2.9); 9.261(2.6); 9.155(3.5); 8.217(3.8); 4.068(0.4); 4.050(0.4);4.000(16.0); 3.944(1.2); 3.926(3.8); 3.907(3.8); 3.889(1.2); 3.440(1.1);3.422(3.6); 3.403(3.7); 3.385(1.2); 2.463(0.6); 2.249(0.4); 2.230(0.4);2.144(556.5); 2.119(2.0); 2.113(2.2); 2.107(2.5); 2.101(1.7);2.095(0.9); 1.971(2.3); 1.964(9.6); 1.952(134.3); 1.946(247.3);1.940(334.2); 1.933(228.1); 1.927(116.0); 1.780(0.7); 1.774(1.4);1.768(1.8); 1.762(1.3); 1.756(0.6); 1.351(3.8); 1.333(7.7); 1.313(5.9);1.293(7.9); 1.286(1.6); 1.275(5.1); 1.222(0.4); 1.203(0.7); 1.186(0.4);0.908(0.5); 0.881(0.4) 0.000(25.0) Example I′-42: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.531(4.5); 9.255(3.9); 8.638(1.7); 8.616(1.8);8.391(1.6); 8.371(1.8); 8.285(4.2); 8.104(0.8); 8.102(0.9); 8.084(1.6);8.066(1.0); 8.063(1.0); 7.960(1.2); 7.942(1.7); 7.922(0.9); 3.860(16.0);3.386(0.9); 3.319(36.4); 2.854(1.3); 2.835(4.1); 2.817(4.2); 2.798(1.4);2.672(0.4); 2.525(0.8); 2.512(19.0); 2.507(40.4); 2.503(57.2);2.498(44.0); 2.494(22.1); 2.330(0.3); 1.236(0.4); 1.001(4.4);0.983(9.2); 0.964(4.3); 0.008(1.7); 0.000(51.1); −0.008(2.1) ExampleI′-43: ¹H-NMR(400.0 MHz, CDCl₃): δ = 9.131(1.1); 9.111(1.2); 9.108(1.1);9.064(2.8); 9.052(0.4); 9.013(0.6); 8.871(1.0); 8.868(1.2); 8.850(1.1);8.848(1.1); 8.184(0.4); 8.180(0.5); 8.166(1.1); 8.163(1.1); 8.146(1.2);8.137(4.0); 8.124(0.6); 8.120(1.1); 8.116(1.1); 8.103(0.6); 8.099(0.4);7.264(22.4); 5.301(3.3); 4.373(0.4); 4.339(0.5); 4.008(13.2);3.989(2.7); 3.913(0.4); 3.900(0.7); 3.882(2.3); 3.863(2.3); 3.844(0.8);3.778(0.4); 3.760(0.4); 3.416(0.4); 1.619(16.0); 1.501(3.0); 1.492(0.8);1.482(6.3); 1.473(1.5); 1.463(3.0); 1.454(0.7); 1.256(0.9); 0.070(1.9);0.000(3.1) Example I′-44: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.805(5.2);9.277(4.7); 8.954(2.1); 8.933(2.2); 8.518(1.9); 8.498(2.1); 8.248(5.0);8.194(0.9); 8.176(1.7); 8.156(1.1); 8.060(1.5); 8.041(2.0); 8.022(1.1);5.755(0.6); 3.886(16.0); 3.785(1.4); 3.766(1.4); 3.320(25.3);2.672(0.4); 2.507(44.1); 2.503(58.0); 2.500(45.6); 2.330(0.4);1.280(4.0); 1.261(8.3); 1.243(3.8); 0.001(13.6); 0.000(14.1) ExampleI′-45: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 9.884(6.3); 9.464(1.7);9.458(1.8); 9.450(1.8); 9.444(1.7); 8.955(1.5); 8.949(1.6); 8.927(1.7);8.921(1.6); 8.858(2.4); 8.854(2.4); 8.606(2.5); 8.601(2.4); 8.083(1.7);8.069(1.6); 8.055(1.6); 8.041(1.6); 7.906(0.4); 7.899(0.4); 7.546(0.4);5.756(0.9); 3.977(1.0); 3.952(3.2); 3.927(3.3); 3.902(1.0); 3.745(16.0);3.316(7.7); 2.514(4.6); 2.509(8.9); 2.503(11.6); 2.497(8.0); 1.235(0.8);1.182(3.7); 1.158(8.1); 1.133(3.5); 0.000(5.7) Example I-46:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 10.312(1.0); 9.681(6.0); 8.972(0.9);8.800(9.0); 8.368(11.7); 8.164(0.4); 8.143(0.4); 8.075(0.5); 8.055(0.5);8.019(3.2); 8.003(3.3); 7.999(3.8); 7.987(3.3); 7.811(0.3); 7.793(0.5);7.748(1.6); 7.745(1.6); 7.731(2.4); 7.728(3.0); 7.710(2.0); 7.707(1.8);7.655(2.3); 7.652(2.2); 7.635(3.2); 7.617(1.7); 7.084(1.3); 5.758(1.2);3.322(39.8); 3.157(2.1); 3.139(6.9); 3.120(7.0); 3.102(2.3); 2.676(0.7);2.672(1.0); 2.668(0.8); 2.525(2.2); 2.507(132.8); 2.503(172.9);2.498(123.6); 2.334(0.8); 2.329(1.0); 2.325(0.8); 1.990(0.9);1.398(1.7); 1.360(0.5); 1.352(0.8); 1.340(7.8); 1.321(16.0); 1.303(7.5);1.274(0.3); 1.259(1.2); 1.250(0.7); 1.232(1.8); 1.193(0.5); 1.175(0.9);1.158(0.5); 0.853(0.5); 0.842(0.3); 0.835(0.4); 0.147(0.4); 0.008(2.7);0.000(87.3); − 0.007(3.3); −0.008(3.3); −0.149(0.4) Example I′-47:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.806(4.4); 8.956(1.8); 8.934(1.9);8.873(2.7); 8.611(2.7); 8.515(1.7); 8.495(1.8); 8.192(0.9); 8.174(1.5);8.155(1.0); 8.153(1.1); 8.057(1.3); 8.038(1.8); 8.019(0.9); 4.038(0.3);3.828(0.7); 3.808(1.9); 3.783(16.0); 3.752(0.5); 3.701(0.9); 3.645(0.4);3.626(0.4); 3.323(184.7); 2.671(1.2); 2.506(162.5); 2.502(211.5);2.498(167.4); 2.329(1.2); 1.988(1.4); 1.398(0.6); 1.339(0.4);1.321(0.9); 1.292(4.0); 1.273(8.1); 1.255(4.0); 1.235(1.6); 1.220(0.9);1.207(0.4); 1.201(0.5); 1.192(0.5); 1.175(0.8); 1.157(0.4); 0.981(0.4);0.146(0.9); −0.001(180.5); −0.150(0.9) Example I′-48: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 9.809(4.1); 9.654(0.3); 8.956(1.7); 8.934(1.8);8.808(2.5); 8.804(2.5); 8.571(2.6); 8.567(2.5); 8.517(1.6); 8.497(1.7);8.195(0.8); 8.177(1.4); 8.158(1.0); 8.061(1.2); 8.041(1.8); 8.023(0.9);4.045(1.1); 3.825(0.7); 3.806(1.9); 3.788(16.0); 3.369(11.9);2.671(1.1); 2.506(157.0); 2.502(197.3); 2.498(147.4); 2.329(1.2);1.989(0.4); 1.453(0.6); 1.398(1.1); 1.290(3.5); 1.271(7.5); 1.253(3.6);1.236(2.1); 0.146(0.5); 0.008(6.4); 0.000(105.6); −0.149(0.5) ExampleI′-49: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.806(4.7); 9.299 (4.4);8.951(1.9); 8.929(2.1); 8.517(1.7); 8.498(1.9); 8.272(4.6); 8.196(0.9);8.178(1.6); 8.157(1.1); 8062(1.4); 8.043(1.9); 8.024(1.0); 4.038(0.4);4.020(0.4); 3.884(16.0); 3.782(1.3); 3.764(1.3); 3.335(11.1);2.671(0.9); 2.506(123.8); 2.502(160.6); 2.498(121.6); 2.329(0.9);1.989(1.6); 1.277(4.1); 1.259(8.7); 1.240(4.5); 1.193(0.4); 1.175(0.8);1.157(0.4); 0.146(0.4); 0.008(4.6); 0.000(90.8); −0.150(0.4) ExampleI′-50: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.654(5.0); 9.326 (4.5);9.234(1.5); 9.213(1.5); 8.453(1.7); 8.433(1.8); 8.323(4.9); 8.066(0.9);8.048(1.7); 8.031(1.3); 8.027(1.3); 7.996(1.5); 7.978(1.8); 7.959(0.8);4.105(16.0); 4.038(0.4); 3.884(0.3); 3.767(0.7); 3.749(0.9); 3.735(1.4);3.717(1.3); 3.698(0.4); 3.684(0.4); 3.666(1.3); 3.647(1.4); 3.634(0.8);3.628(0.5); 3.615(0.7); 3.323(114.7); 2.675(1.0); 2.671(1.4);2.666(1.0); 2.506(178.7); 2.502(236.7); 2.497(177.5); 2.333(1.0);2.329(1.3); 2.324 (1.0); 1.989(1.5); 1.435(3.9); 1.416(8.3); 1.398(3.9);1.259(0.7); 1.234(0.7); 1.193(0.4); 1.175(0.8); 1.157(0.4); 0.146(0.6);0.008(6.3); 0.000(145.6); −0.008(7.2); −0.150(0.6) Example I′-51:¹H-NMR(400.1.MHz, d₆-DMSO): δ = 9.990(4.2); 9.839(0.4); 9.166(1.5);9.144(1.7); 9.048(2.3); 8.896(2.4); 8.893(2.4); 8.644(2.5); 8.640(2.5);8.450(1.4); 8.445(1.3); 8.427(1.3); 8.422(1.3); 4.086(1.3); 3.886(0.6);3.867(1.8); 3.849(1.8); 3.830(0.7); 3.803(16.0); 3.325(50.7);3.301(0.6); 2.511(16.3); 2.507(32.4); 2.502(42.6); 2.498(30.2);1.989(0.3); 1.505(0.6); 1.310(3.7); 1.292(8.1); 1.273(3.7); 1.234(2.0);0.940(0.3); 0.008(1.1); 0.000(27.8); −0.008(1.1) Example I′-52:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.796(4.4); 9.286(4.0); 8.949(1.7);8.928(1.9); 8.518(1.6); 8.497(1.7); 8.245(4.3); 8.202(0.8); 8.199(0.9);8.185(1.1); 8.181(1.5); 8.163(1.0); 8.160(1.0); 8.061(1.2); 8.043(1.8);8.024(0.9); 5.757(7.5); 4.122(0.7); 4.039(0.3); 4.021(0.3); 3.924(16.0);3.643(15.0); 3.430(0.7); 3.327(44.1); 2.512(14.8); 2.508(29.0);2.503(38.1); 2.499(28.3); 1.990(1.5); 1.193(0.4); 1.175(0.8);1.158(0.4); 0.008(2.2); 0.000(43.4); −0.008(1.8) Example I′-53:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.839(4.4); 8.941(1.7); 8.920(1.9);8.714(6.3); 8.549(1.6); 8.529(1.7); 8.232(0.8); 8.229(0.8); 8.214(1.1);8.211(1.6); 8.193(1.0); 8.189(1.0); 8.095(1.2); 8.075(1.8); 8.057(0.9);4.039(0.5); 4.021(0.6); 4.003(0.4); 3.990(16.0); 3.639(14.8);3.321(26.3); 2.525(0.9); 2.511(17.4); 2.507(35.5); 2.503(48.7);2.498(37.1); 1.989(2.2); 1.193(0.6); 1.175(1.2); 1.158(0.6); 0.008(2.0);0.000(52.4); −0.008(2.1) Example I′-54: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =9.847(4.7); 8.937(1.8); 8.916(2.0); 8.717(6.4); 8.549(1.7); 8.529(1.8);8.226(0.8); 8.223(0.9); 8.208(1.2); 8.205(1.6); 8.186(1.0); 8.183(1.0);8.091(1.3); 8.073(1.9); 8.054(0.9); 3.952(16.0); 3.781(0.7); 3.762(1.9);3.744(1.9); 3.726(0.7); 3.320(59.5); 2.675(0.5); 2.671(0.6); 2.667(0.5);2.506(72.1); 2.502(98.9); 2.498(76.0); 2.333(0.4); 2.329(0.6);2.325(0.5); 1.989(1.0); 1.398(0.9); 1.277(3.8); 1.259(8.2); 1.240(3.8);1.175(0.5); 0.146(0.4); 0.008(3.6) 0.000(90.1); −0.008(4.1); −0.150(0.4)Example I-55: ¹H-NMR(600.1 MHz, d₆-DMSO): δ = 9.449(6.4); 9.348(6.1);9.249(9.4); 8.769(10.1); 8.577(5.6); 8.573(5.7); 8.217(4.2); 8.202(5.2);8.074(3.6); 8.070(3.6); 8.059(3.0); 8.055(3.0); 4.175(2.1); 4.163(7.0);4.150(7.0); 4.138(2.2); 4.025(0.3); 3.327(87.0); 2.617(0.4); 2.526(0.8);2.523(1.0); 2.520(1.2); 2.508(46.7); 2.505(63.1); 2.502(48.2);2.389(0.4); 1.991(1.4); 1.397(1.5); 1.307(7.4); 1.295(16.0); 1.282(7.3);1.188(0.4); 1.176(0.7); 1.165(0.4); 0.005(0.5); 0.000(11.7) ExampleI-56: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.467(6.2); 9.350(6.1);9.302(9.1); 8.754(10.4); 8.480(5.2); 8.458(5.7); 8.337(0.7); 8.315(0.7);8.280(4.9); 8.275(5.1); 7.918(3.6); 7.913(3.5); 7.896(3.4); 7.891(3.4);7.720(0.3); 7.699(0.4); 7.355(0.4); 7.350(0.4); 7.299(0.5); 7.283(0.7);7.272(0.4); 7.262(0.7); 4.180(1.9); 4.161(6.7); 4.143(6.8); 4.124(2.0);4.038(0.4); 4.020(0.5); 3.318(243.1); 2.689(0.4); 2.675(2.1);2.671(2.9); 2.666(2.2); 2.524(9.5); 2.510(168.3); 2.506(345.7);2.502(476.8); 2.497 (360.5); 2.493(179.4); 2.333(2.0); 2.328(2.8);2.324(2.0); 1.989(2.0); 1.649(0.8); 1.398(0.7); 1.315(7.2); 1.296(16.0);1.278(7.0); 1.236(0.7); 1.193(0.5); 1.175(1.0); 1.157(0.5); 1.105(0.3);0.146(1.9); 0.008(15.6); 0.000(415.4); −0.008(16.8); −0.150(1.8) ExampleI-57: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.449(6.0); 9.345(5.9);9.246(9.0); 8.767(10.0); 8.418(3.1); 8.399(3.2); 8.212(3.0); 8.190(4.0);8.088(1.9); 8.084(2.0); 8.071(2.4); 8.067(3.3); 8.063(1.8); 8.049(1.7);8.046(1.7); 7.877(2.0); 7.874(2.2); 7.857(3.5); 7.839(1.7); 7.837(1.7);4.177(2.0); 4.159(6.7); 4.140(6.8); 4.122(2.0); 3.321(82.5); 2.676(0.6); 2.672(0.8); 2.667(0.6); 2.525(2.6); 2.512(45.0); 2.507(93.8);2.503(130.7); 2.498(100.0); 2.494(50.3); 2.334(0.6); 2.330(0.8);2.325(0.6); 2.075(3.4); 1.316(7.1); 1.297(16.0); 1.279(7.0); 1.233(0.5);0.146(0.6); 0.008(5.0); 0.000(132.8); −0.008(5.6); −0.150(0.6) ExampleI′-58: ¹H-NMR(601.6 MHz, d₆-DMSO): δ = 9.774(4.2); 8.964(1.7);8.950(1.8); 8.488(1.6); 8.475(1.6); 8.165(0.8); 8.163(0.8); 8.153(1.1);8.151(1.6); 8.149(1.0); 8.139(1.0); 8.137(0.9); 8.068(2.6); 8.027(1.1);8.015(1.8); 8.003(0.9); 7.937(1.8); 7.923(2.0); 7.712(1.5); 7.710(1.5);7.698(1.3); 7.696(1.3); 4.036(0.4); 4.024(0.4); 3.819(0.8); 3.780(16.0);3.307(52.0); 2.615(0.6); 2.612(0.8); 2.609(0.6); 2.521(1.6); 2.518(2.1);2.515(2.4); 2.506(49.3); 2.503(98.4); 2.500(132.6); 2.497(99.9);2.495(50.3); 2.387(0.6); 2.384(0.8); 2.381(0.6); 1.988(1.7); 1.907(1.0);1.287(3.8); 1.274(8.1); 1.262(3.8); 1.235(0.5); 1.187(0.5); 1.175(0.9);1.163(0.5); 0.005(1.4); 0.000(33.4); −0.006(1.5) Example I-59:¹H-NMR(601.6 MHz, d₆-DMSO): δ = 9.313(3.6); 8.347(3.0); 8.331(3.3);8.324(3.9); 7.870(1.7); 7.865(1.8); 7.854(1.6); 7.850(1.7); 7.741(2.9);7.737(2.7); 4.060(15.2); 3.968(16.0); 3.776(1.1); 3.763(3.8);3.751(3.9); 3.739(1.2); 3.309(240.8); 3.281(0.4); 2.615(0.8);2.612(1.1); 2.609(0.8); 2.521(2.2); 2.518(2.7); 2.515(2.9); 2.506(66.9);2.503(136.7); 2.500(184.0); 2.497(137.4); 2.495(66.9); 2.388(0.8);2.385(1.1); 2.382(0.8); 2.072(0.9); 1.255(4.1); 1.243(8.8); 1.230(4.0);0.005(1.4); 0.000(37.9); −0.006(1.5)

APPLICATION EXAMPLES

Ctenocephalides felis—In Vitro Contact Tests with Adult Cat Fleas

For the coating of the test tubes, 9 mg of active ingredient are firstdissolved in 1 ml of acetone p.a. and then diluted to the desiredconcentration with acetone p.a. 250 μl of the solution are distributedhomogeneously on the inner walls and the base of a 25 ml test tube byturning and rocking on an orbital shaker (rocking rotation at 30 rpm for2 h). With 900 ppm active ingredient solution and internal surface area44.7 cm², given homogeneous distribution, an area-based dose of 5 μg/cm²is achieved.

After the solvent has evaporated off, the tubes are populated with 5-10adult cat fleas (Ctenocephalides felis), sealed with a perforatedplastic lid and incubated in a horizontal position at room temperatureand ambient humidity. After 48 h, efficacy is determined. To this end,the test tubes are stood upright and the fleas are knocked to the baseof the tube. Fleas which remain motionless at the base or move in anuncoordinated manner are considered to be dead or moribund.

A substance shows good efficacy against Ctenocephalides felis if atleast 80% efficacy was achieved in this test at an application rate of 5μg/cm². 100% efficacy means that all the fleas were dead or moribund. 0%efficacy means that no fleas were harmed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 5 μg/cm²(=500 g/ha): I-1

Ctenocephalides felis—Oral Test

Solvent: dimethyl sulphoxide

For the purpose of production of a suitable active ingredientpreparation, 10 mg of active ingredient are mixed with 0.5 ml ofdimethyl sulphoxide. Dilution with citrated cattle blood gives thedesired concentration.

About 20 unfed adult cat fleas (Ctenocephalides felis) are placed into achamber which is closed at the top and bottom with gauze. A metalcylinder whose bottom end is closed with parafilm is placed onto thechamber. The cylinder contains the blood/active ingredient preparation,which can be imbibed by the fleas through the parafilm membrane.

After 2 days, the kill in % is determined. 100% means that all of thefleas have been killed; 0% means that none of the fleas have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm: I-1

Lucilia cuprina Test

Solvent: dimethyl sulphoxide

To produce a suitable active ingredient preparation, 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration.

About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) aretransferred into a test vessel containing minced horsemeat and theactive ingredient preparation of the desired concentration.

After 2 days, the kill in % is determined. 100% means that all thelarvae have been killed; 0% means that no larvae have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm: I-1

Musca domestica Test

Solvent: dimethyl sulphoxide

To produce a suitable active ingredient preparation, 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration.

Vessels containing a sponge treated with sugar solution and the activeingredient preparation of the desired concentration are populated with10 adult houseflies (Musca domestica).

After 2 days, the kill in % is determined. 100% means that all of theflies have been killed; 0% means that none of the flies have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 75% at an application rate of 4 ppm: I-1

Meloidogyne incognita Test

Solvent: 125.0 parts by weight of acetone

To produce a suitable preparation of active ingredient, 1 part by weightof active ingredient is mixed with the stated amount of solvent and theconcentrate is diluted with water to the desired concentration.

Vessels are filled with sand, active ingredient solution, an egg/larvaesuspension of the southern root-knot nematode (Meloidogyne incognita)and lettuce seeds. The lettuce seeds germinate and the plants develop.The galls develop on the roots.

After 14 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls were found; 0% means thatthe number of galls on the treated plants corresponds to the untreatedcontrol.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 ppm: I-32

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 20 ppm: I-40

In this test, for example, the following compounds from the preparationexamples show an efficacy of 70% at an application rate of 20 ppm: I-1

Myzus persicae—Spray Test

Solvent: 78 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient preparation, 1 part by weight ofactive ingredient is dissolved with the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive ingredient preparation of the desired concentration.

After 5-6 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha:I-13

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 500 g/ha:I-6, I-7, I-8, I-10, I-12, I-14, I-16, I-17, I-41, I′-42, I′-44

In this test, for example, the following compounds from the preparationexamples show an efficacy of 70% at an application rate of 500 g/ha:I-5, I-11, I-30

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-2, I-18, I-20, I-21, I-22, I-23

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 g/ha:I-1, I-19

Phaedon cochleariae—Spray Test

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient preparation, 1 part by weight ofactive ingredient is dissolved with the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active ingredient preparation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the efficacy in % is determined. 100% means that all thebeetle larvae have been killed; 0% means that no beetle larvae have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha:I-1, I-5, I-7, I-8, I-10, I-11, I-12, I-14, I-15, I-16, I-17, I-25

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 500 g/ha:I-6, I-30, I-35, I′-44

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-13, I-18, I-19, I-20, I-21, I-23

Spodoptera frugiperda—Spray Test

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient preparation, 1 part by weight ofactive ingredient is dissolved with the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Leaf discs of maize (Zea mays) are sprayed with an active ingredientpreparation of the desired concentration and, after drying, populatedwith caterpillars of the armyworm (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined. 100% means that all thecaterpillars have been killed; 0% means that no caterpillar has beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha:I-1, I-2, I-5, I-6, I-7, I-8, I-10, I-11, I-12, I-14, I-15, I-16, I-17,I-25, I-30, I-35, I′-44

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 500 g/ha:I-13

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-19, I-18, I-20, I-21, I-22, I-23

Tetranychus urticae—Spray Test, OP-Resistant

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient preparation, 1 part by weight ofactive ingredient is dissolved with the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of bean leaves (Phaseolus vulgaris) infested with all stages ofthe greenhouse red spider mite (Tetranychus urticae) are sprayed with anactive ingredient preparation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that no spider mites have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 70% at an application rate of 500 g/ha:I′-42

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 100% at an application rate of 100 g/ha:I-34

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 90% at an application rate of 100 g/ha:I-22, I-36, I-37

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 70% at an application rate of 100 g/ha:I-4, I-18, I-29

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 100% at an application rate of 20 g/ha:I-23

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 70% at an application rate of 20 g/ha:I-21, I-40

The invention claimed is:
 1. A compound of formula (I) or (I′)

wherein Aa is nitrogen or ═C(R⁷)—, Ab is nitrogen or ═C(H)—, Ac isnitrogen or ═C(H)—, Ad is nitrogen or ═C(H)—, Ae is nitrogen or ═C(H)—,where Ab, Ac, Ad and Ae cannot all be nitrogen, R¹ is (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, amino, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)haloalkylthio-(C₁-C₆)-alkyl,(C₁-C₆)alkylsulphinyl-(C₁-C₆)-alkyl,(C₁-C₆)haloalkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl-(C₁-C₆)-alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonylamino,aminosulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl,di-(C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl, or (C₁-C₆)alkyl,(C₁-C₆)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, eachoptionally mono- or polysubstituted identically or differently by aryl,hetaryl or heterocyclyl, where aryl, hetaryl or heterocyclyl may eachoptionally be mono- or polysubstituted identically or differently byhalogen, cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl,aminosulphonyl, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,(C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl, (C₁-C₆)alkylsulphimino,(C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulphoximino,(C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl or benzyl, or R¹ is aryl,hetaryl or heterocyclyl, each mono- or polysubstituted identically ordifferently by halogen, cyano, nitro, hydroxyl, amino, carboxyl,carbamoyl, (C₁-C₆)alkyl, (C₃-C₈)cycloalkyl, (C₁-C₆)-alkoxy,(C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,(C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl, (C₁-C₆)alkylsulphimino,(C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulphoximino,(C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl, (═O) (in the case ofheterocyclyl only) and (═O)₂ (in the case of heterocyclyl only), R², R³are independently hydrogen, cyano, halogen, nitro, acetyl, hydroxyl,amino, SCN, tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,(C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di-(C₁-C₆)alkylaminocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,(C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, aminosulphonyl,(C₁-C₆)alkylaminosulphonyl, di-(C₁-C₆)alkylaminosulphonyl,(C₁-C₆)alkylsulphoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino or NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino),R⁷ is hydrogen, cyano, halogen, acetyl, hydroxyl, amino,(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkylsulphinyl,(C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkylsulphonyl or(C₁-C₆)haloalkylsulphonyl, Q is a partly saturated or saturatedheterocyclic or heteroaromatic 8-, 9-, 10-, 11- or 12-membered fusedbicyclic or tricyclic ring system, where at least one carbonyl group mayoptionally be present and/or where the ring system is optionally mono-or polysubstituted identically or differently, and where thesubstituents may independently be selected from hydrogen, cyano,halogen, nitro, acetyl, hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl,(C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,(C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₄)alkyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,(C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylthiocarbonyl, (C₁-C₆)haloalkylcarbonyl,(C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)alkylaminocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminocarbonyl,di-(C₁-C₆)alkylaminothiocarbonyl, (C₂-C₆)alkenylaminocarbonyl,di-(C₂-C₆)-alkenylaminocarbonyl, (C₃-C₈)cycloalkylaminocarbonyl,(C₁-C₆)alkylsulphonylamino, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino,aminosulphonyl, (C₁-C₆)alkylaminosulphonyl,di-(C₁-C₆)alkylaminosulphonyl, (C₁-C₆)alkylsulphoximino,aminothiocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di-(C₁-C₆)alkylaminothiocarbonyl, (C₃-C₈)cycloalkylamino,NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino), or where the substituentsmay independently be selected from phenyl or a 5- or 6-memberedheteroaromatic ring, where phenyl or the ring may optionally be mono- orpolysubstituted identically or differently by C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,NO₂, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, n is 0, 1 or 2, where, in the caseof the structural unit A4, Q is none of the following ring systems:

 where X and Y, which may be the same or different, are carbon ornitrogen, R′″ is hydrogen, aldehyde, oxime or —C(O)O—R_(a), with theproviso that X is carbon, where R_(a) is C₁-C₆-alkyl, R′ and R″, whichmay be the same or different, are hydrogen, halogen, cyano, nitro,C₁-C₆-alkyl or C₁-C₆-alkoxy, and, in addition, when Aa is ═C(H)—, in thecase of the compounds of the formula (I), Q is not Q1, Q2, Q3, Q4, Q5,Q6, Q7, Q8, Q9, Q10, Q15, or Q17; with the proviso that the compound offormula (I) or (I′) is not


2. The compound of formula (I) or (I′) according to claim 1, wherein Aais nitrogen or ═C(R⁷)—, Ab is nitrogen or ═C(H)—, Ac is nitrogen or═C(H)—, Ad is nitrogen or ═C(H)—, Ae is nitrogen or ═C(H)—, where Ab,Ac, Ad and Ae cannot all be nitrogen, optionally resulting in one of thefollowing structural units A1 to A44:

where the bond to the substituent Q is identified by a wavy line and thebond to the sulphur atom by an asterisk *, R¹ is (C₁-C₄)alkyl,(C₁-C₄)hydroxyalkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,(C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,(C₃-C₆)cycloalkylamino, (C₁-C₄)alkylcarbonylamino,(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylsulphinyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylcarbonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonylamino, or is(C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl,(C₃-C₆)cycloalkyl, each optionally mono- or disubstituted identically ordifferently by aryl, hetaryl and heterocyclyl, where aryl, hetaryl andheterocyclyl may each optionally be mono- or disubstituted identicallyor differently by halogen, cyano, carbamoyl, aminosulphonyl,(C₁-C₄)-alkyl, (C₃-C₄)cycloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkyl,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl,(C₁-C₄)alkylsulphonyl, (C₁-C₄)alkylsulphimino, or R¹ is optionally aryl,hetaryl or heterocyclyl, each optionally mono- or disubstitutedidentically or differently by halogen, cyano, carbamoyl, (C₁-C₄)alkyl,(C₃-C₆)cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl,(C₁-C₄)alkylsulphimino, (C₁-C₄)alkylsulphoximino, (C₁-C₄)alkylcarbonyl,(C₃-C₄)trialkylsilyl, (═O) (in the case of heterocyclyl only) or (═O)₂(in the case of heterocyclyl only), R², R³ are independently hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl,(C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,(C₁-C₄)haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl,(C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,aminosulphonyl, (C₁-C₄)alkylaminosulphonyl,di-(C₁-C₄)alkylaminosulphonyl, aminothiocarbonyl or NHCO—(C₁-C₄)alkyl((C₁-C₄)alkylcarbonylamino), R⁷ is hydrogen, cyano, halogen, acetyl,hydroxyl, amino, (C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,(C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,(C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl or(C₁-C₄)haloalkylsulphonyl, Q is a heteroaromatic 8-, 9-, 10-, 11- or12-membered fused bicyclic or tricyclic ring system, where the ringsystem is optionally mono- or polysubstituted identically ordifferently, and where the substituents may independently be selectedfrom hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri-(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₆)haloalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphinyl, (C₁-C₆)haloalkylsulphinyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphonyl, (C₁-C₆)haloalkylsulphonyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl, (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphonyloxy, (C₁-C₆)alkylcarbonyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di-(C₁-C₆)alkylaminocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,(C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, aminosulphonyl,(C₁-C₆)alkylaminosulphonyl, di-(C₁-C₆)alkylaminosulphonyl,(C₁-C₆)alkylsulphoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino),or where the substituents may independently be selected from phenyl or a5- or 6-membered heteroaromatic ring, where phenyl or the ring mayoptionally be mono- or polysubstituted identically or differently byC₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, n is0, 1 or 2, where, in the case of the structural unit A4, Q is none ofthe following ring systems:

 where X and Y, which may be the same or different, are carbon ornitrogen, R′″ is hydrogen, aldehyde, oxime or —C(O)O—R_(a), with theproviso that X is carbon, where R_(a) is C₁-C₆-alkyl, R′ and R″, whichmay be the same or different, are hydrogen, halogen, cyano, nitro,C₁-C₆-alkyl or C₁-C₆-alkoxy, and, in addition, when Aa is ═C(H)—, in thecase of the compounds of the formula (I), Q is not Q1, Q2, Q3, Q4, Q5,Q6, Q7, Q8, Q9, Q10, Q15, or Q17.
 3. The compound of formula (I) or (I′)according to claim 1, wherein Aa is nitrogen or ═C(R⁷)—, Ab is nitrogenor ═C(H)—, Ac is nitrogen or ═C(H)—, Ad is nitrogen or ═C(H)—, Ae isnitrogen or ═C(H)—, where Ab, Ac, Ad and Ae cannot all be nitrogen,optionally resulting in one of the following structural units: A1, A2,A3, A4, A5, A7, A8, A9, A10, A11, A12, A13, A14, A15, A17, A19, A20,A21, A22, A23, A24, A25, A26, A27, A29, A30, A31, A32, A33, A34, A35,A36, A37, A39, A41, A42, A43, or A44, R¹ is (C₁-C₄)-alkyl,(C₁-C₄)hydroxyalkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl,(C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,(C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl or(C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl, R², R³ are independently hydrogen,cyano, halogen, nitro, hydroxyl, amino, SCN, tri-(C₁-C₄)alkylsilyl,(C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkylhydroxyimino,(C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,(C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkylsulphonyl,(C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,(C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulphonylamino,(C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino, aminosulphonyl,(C₁-C₄)alkylaminosulphonyl, di-(C₁-C₄)alkylaminosulphonyl orNHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino), R⁷ is hydrogen, halogen,cyano, (C₁-C₄)alkyl or (C₁-C₄)haloalkyl, Q is a heteroaromatic9-membered or 12-membered fused bicyclic or tricyclic ring systemselected from the group consisting of Q1 to Q20

R⁴ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,(C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,(C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkylor (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, R⁵, R⁶ are independently hydrogen,cyano, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl,(C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,(C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,(C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl,(C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyloxy,(C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,(C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,aminosulphonyl, (C₁-C₄)alkylaminosulphonyl ordi-(C₁-C₄)alkylaminosulphonyl, n is 0, 1 or 2, where, when Aa is ═C(H)—,in the case of the compounds of the formula (I), Q is not Q1, Q2, Q3,Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q15, or Q17.
 4. The compound of formula (I)or (I′) according to claim 1, wherein Aa is nitrogen or ═C(R⁷)—, Ab isnitrogen or ═C(H)—, Ac is nitrogen or ═C(H)—, Ad is nitrogen or ═C(H)—,Ae is nitrogen or ═C(H)—, where Ab, Ac, Ad and Ae cannot all benitrogen, optionally resulting in one of the following structural units:A1, A2, A4, A5, A7, A9, A11, A12, A13, A19, A20, A21, A22, A23, A24,A26, A27, A29, A31, A33, A34, A35, A41, A42, A43, or A44, R¹ is(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl or (C₃-C₆)-cycloalkyl, R², R³ areindependently hydrogen, cyano, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkylthio,(C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl orNHCO—(C₁-C₄)-alkyl ((C₁-C₄)-alkylcarbonylamino), R⁷ is hydrogen,halogen, cyano, (C₁-C₄)alkyl or (C₁-C₄)haloalkyl, Q is a heteroaromatic9-membered or 12-membered fused bicyclic or tricyclic ring systemselected from the group consisting of Q1, Q2, Q3, Q5, Q6, Q8, Q9, Q10,Q11, Q12, Q13, Q15, Q16, Q17, Q18, Q19 and Q20, R⁴ is hydrogen,(C₁-C₄)alkyl or (C₁-C₄)-alkoxy-(C₁-C₄)alkyl, R⁵ is hydrogen, cyano,halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,(C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylcarbonyl,(C₁-C₄)haloalkylcarbonyl, (C₁-C₄)alkylaminocarbonyl,di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulphonylamino,(C₁-C₄)alkylaminosulphonyl or di-(C₁-C₄)alkylaminosulphonyl, R⁶ ishydrogen, n is 0, 1 or 2, where, when Aa is ═C(H)—, in the case of thecompounds of the formula (I), Q is not Q1, Q2, Q3, Q5, Q6, Q8, Q9, Q10,Q15, or Q17.
 5. The compound of the formula (I) or (I′) according toclaim 1, wherein Aa is nitrogen or ═C(R⁷)—, Ab is ═C(H)—, Ac is ═C(H)—,Ad is ═C(H)—, Ae is nitrogen or ═C(H)—, resulting in one of thefollowing structural units: A1, A4, A23, A26, or A33, R¹ is methyl,ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl,cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl, R²,R³ are independently hydrogen, fluorine, chlorine, bromine, iodine,cyano, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy ortrifluoromethylthio, R⁷ is hydrogen, fluorine, chlorine, bromine, cyano,methyl, ethyl or trifluoromethyl, Q is a heteroaromatic 9-membered fusedbicyclic ring system selected from the group consisting of Q1, Q2, Q3,Q16, Q17 and Q20, R⁴ is hydrogen, methyl, ethyl, isopropyl,methoxymethyl or methoxyethyl, R⁵ is fluorine, chlorine, bromine,fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂,CHFCH₃), difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl,(CH₂CF₃, CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphanyl, R⁶ is hydrogen, n is 0, 1 or 2, where, when Aais ═C(H)—, in the case of the compounds of the formula (I), Q is not Q1,Q2, Q3, or Q17.
 6. The compound of formula (I) or (I′) according toclaim 1, wherein Aa is nitrogen or ═C(R⁷)—, Ab is ═C(H)—, Ac is ═C(H)—,Ad is ═C(H)—, Ae is nitrogen or ═C(H)—, resulting in one of thefollowing structural units: A1, A4, A23, A26, or A33 R¹ is methyl orethyl, R² is hydrogen, chlorine, methoxy or trifluoromethyl, R³ ishydrogen, R⁷ is hydrogen, Q is a heteroaromatic 9-membered or12-membered fused bicyclic ring system selected from the groupconsisting of Q1, Q2, Q3, Q16, Q17, and Q20, R⁴ is hydrogen or methyl,R⁵ is trifluoromethyl or pentafluoroethyl, R⁶ is hydrogen, n is 0, 1 or2, where, when Aa is ═C(H)—, in the case of the compounds of the formula(I), Q is not Q1, Q2, Q3, or Q17.
 7. The compound of the formula (I′)according to claim
 1. 8. The compound of formula (I) or (I′) accordingto claim 1, selected from the group consisting of I-3, I-4, I-6, I-7,I-8, I-9, I-10, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21,I-23, I-24, I-27, I-28, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36,I-37, I-38, I-40, I-41, I′-42, I′-43, I′-44, I′-45, I′-47, I′-48, I′-49,I′-50, I′-51, I′-52, I′-53, I′-54, I-55, I-56, I-57, I′-58, I-59,


9. A compound of formula (III-1)


10. The compound of formula (I′) according to claim 7, wherein Q is


11. The compound of formula (I′) according to claim 7, wherein n is 2.12. The compound of formula (I′) according to claim 7, wherein R¹ isethyl.
 13. The compound of formula (I′) according to claim 7, wherein R⁴is methyl.
 14. The compound of formula (I′) according to claim 7,wherein Aa is ═C(R⁷)—, and R⁷ is hydrogen.
 15. The compound of formula(I′) according to claim 7, wherein Ab, Ac, Ad, and Ae are each ═C(H)—.16. An agrochemical formulation comprising one or more compounds offormula (I) or formula (I′) according to claim 1 and also one or moreextenders and/or surfactants.
 17. The agrochemical formulation accordingto claim 16, additionally comprising a further active agrochemicalingredient.
 18. A method for controlling one or more animal pests,comprising allowing a compound of formula (I) or formula (I′) accordingto claim 1 or an agrochemical formulation thereof to act on the animalpests and/or a habitat thereof.
 19. A product comprising the compound offormula (I) or formula (I′) according to claim 1 or an agrochemicalformulation thereof for controlling one or more animal pests.